Product Name

  • Name

    7-Methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4(3H)-one

  • EINECS 429-400-7
  • CAS No. 199327-61-2
  • Article Data25
  • CAS DataBase
  • Density 1.327 g/cm3
  • Solubility
  • Melting Point 233-236 °C
  • Formula C16H21N3O4
  • Boiling Point 519.53 °C at 760 mmHg
  • Molecular Weight 319.36
  • Flash Point 268.002 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 199327-61-2 (7-Methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4(3H)-one)
  • Hazard Symbols
  • Synonyms 4(1H)-Quinazolinone,7-methoxy-6-[3-(4-morpholinyl)propoxy]- (9CI);4(3H)-Quinazolinone,7-methoxy-6-[3-(4-morpholinyl)propoxy]-;
  • PSA 76.68000
  • LogP 0.97070

Synthetic route

C9H6N2O3(2-)*2Na(1+)

C9H6N2O3(2-)*2Na(1+)

4 (3-bromopropyl)-morpholine
125422-83-5

4 (3-bromopropyl)-morpholine

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
With 1-butyl-3-methylimidazolium Tetrafluoroborate In tetrahydrofuran at 65 - 70℃; for 5h;93.8%
4-(3-chloropropyl)morpholine
7357-67-7

4-(3-chloropropyl)morpholine

C9H6N2O3(2-)*2K(1+)

C9H6N2O3(2-)*2K(1+)

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
With 1-butyl-3-methylimidazolium Tetrafluoroborate In N,N-dimethyl-formamide at 55 - 60℃; for 5h;93.7%
4-(3-iodopropyl)morpholine
1417436-51-1

4-(3-iodopropyl)morpholine

C9H6N2O3(2-)*2K(1+)

C9H6N2O3(2-)*2K(1+)

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
With 1-butyl-3-methylimidazolium Tetrafluoroborate In N,N-dimethyl-formamide at 75 - 80℃; for 5h;91.2%
formamidine acetic acid
3473-63-0

formamidine acetic acid

methyl 5-(3-morpholinopropoxy)-2-amino-4-methoxy-benzoate
214472-41-0

methyl 5-(3-morpholinopropoxy)-2-amino-4-methoxy-benzoate

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
In ethanol for 4h; Reflux;88%
In methanol at 50 - 60℃; for 6h;81.73%
In 2-methoxy-ethanol at 115℃; for 2h;78%
In methanol at 50 - 60℃; for 6h;
2-amino-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzamide
246512-44-7

2-amino-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzamide

formaldehyd
50-00-0

formaldehyd

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
In water at 130℃; for 48h;88%
7-methoxy-6-(3'-N-morpholino)propoxyquinazoline
1208902-96-8

7-methoxy-6-(3'-N-morpholino)propoxyquinazoline

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
Stage #1: 7-methoxy-6-(3'-N-morpholino)propoxyquinazoline With ammonium cerium (IV) nitrate; acetic acid In water
Stage #2: With sodium hydroxide In water		87%
With peracetic acid; sulfuric acid In ethanol at 60℃; for 12h;85%
2-nitro-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzonitrile
675126-26-8

2-nitro-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzonitrile

formic acid
64-18-6

formic acid

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
Stage #1: 2-nitro-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzonitrile With iron(III) chloride; hydrazine hydrate In methanol; water for 3h; Heating;
Stage #2: formic acid With hydrogenchloride In water at 90 - 130℃; Further stages.;		86%
Stage #1: 2-nitro-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzonitrile With iron(III) chloride; hydrazine hydrate In methanol; water at 80℃; for 3.5h;
Stage #2: formic acid With hydrogenchloride In water at 130℃; for 4h;		68.65%
Stage #1: 2-nitro-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzonitrile With iron(III) chloride; hydrazine hydrate In methanol; water for 3h; Reflux;
Stage #2: formic acid With hydrogenchloride In water at 130℃; for 3.5h;		58%
C16H20N2O6

C16H20N2O6

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
With formamidine acetic acid82%
2-amino-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzamide
246512-44-7

2-amino-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzamide

formic acid
64-18-6

formic acid

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
Stage #1: 2-amino-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzamide; formic acid With formamide at 20 - 100℃;
Stage #2: at 100℃; for 7h;		78%
Stage #1: 2-amino-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzamide; formic acid In dichloromethane at 100℃; for 5h; Acidic conditions;
Stage #2: With hydrogenchloride In water at 70℃; for 3h; Acidic aqueous solution;
Stage #3: With sodium hydroxide In water at 20 - 25℃; Alkaline aqueous solution;
With formamide at 20℃; for 8h; Reflux;3.3 g
ammonium formate
16712-16-6, 64165-14-6, 65387-22-6, 70179-79-2, 540-69-2

ammonium formate

formamide
77287-34-4, 77287-35-5, 60100-09-6

formamide

methyl 5-(3-morpholinopropoxy)-2-amino-4-methoxy-benzoate
214472-41-0

methyl 5-(3-morpholinopropoxy)-2-amino-4-methoxy-benzoate

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
at 170℃; for 3h;71.1%
...Expand
ethyl 2-amino-4-methoxy-5-(3-morpholin-4-ylpropoxy)benzoate
1040264-49-0

ethyl 2-amino-4-methoxy-5-(3-morpholin-4-ylpropoxy)benzoate

formamidine acetic acid
3473-63-0

formamidine acetic acid

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
In 2-methoxy-ethanol for 8h; Heating;69.2%
In methanol for 6h; Reflux;
C16H23N3O5

C16H23N3O5

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
With trichlorophosphate In toluene for 2h; Reflux;40%
4-(3-chloropropyl)morpholine
7357-67-7

4-(3-chloropropyl)morpholine

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 391.5 g / potassium carbonate / dimethylformamide / 3 h / 100 °C
2.1: 391 g / hydroxylamine hydrochloride; pyridine / methanol / 1 h / Heating
3.1: 349 g / acetic anhydride / 3 h / 110 °C
4.1: 329 g / aq. nitric acid / acetic acid / 8 h / 45 - 50 °C
5.1: FeCl3; hydrazine hydrate / H2O; methanol / 3 h / Heating
5.2: 86 percent / HCl / H2O / 90 - 130 °C
View Scheme
Multi-step reaction with 5 steps
1.1: 95 percent / K2CO3 / dimethylformamide / 10 h / 85 °C
2.1: 95 percent / aq. H2SO4; HNO3; AcOH / 50 h / 20 °C
3.1: 75 percent / sodium dithionite / H2O / 20 - 50 °C
4.1: 38 percent / KOH / 2-methyl-butan-2-ol / 82 °C
5.1: formamide / 20 - 100 °C
5.2: 78 percent / 7 h / 100 °C
View Scheme
4-methoxy-3-[3-(morpholin-4-yl)propoxy]benzonitrile
675126-28-0

4-methoxy-3-[3-(morpholin-4-yl)propoxy]benzonitrile

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 329 g / aq. nitric acid / acetic acid / 8 h / 45 - 50 °C
2.1: FeCl3; hydrazine hydrate / H2O; methanol / 3 h / Heating
2.2: 86 percent / HCl / H2O / 90 - 130 °C
View Scheme
Multi-step reaction with 4 steps
1.1: 95 percent / aq. H2SO4; HNO3; AcOH / 50 h / 20 °C
2.1: 75 percent / sodium dithionite / H2O / 20 - 50 °C
3.1: 38 percent / KOH / 2-methyl-butan-2-ol / 82 °C
4.1: formamide / 20 - 100 °C
4.2: 78 percent / 7 h / 100 °C
View Scheme
Multi-step reaction with 4 steps
1: nitric acid; sulfuric acid; acetic acid / 37 h / 0 - 20 °C
2: dihydrogen peroxide; potassium carbonate / dimethyl sulfoxide / 1.5 h / 50 °C
3: palladium on activated charcoal / ethyl acetate; dichloromethane / 1.8 h / Reflux
4: formamide / 8 h / 20 °C / Reflux
View Scheme
isovanillin
621-59-0

isovanillin

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 391.5 g / potassium carbonate / dimethylformamide / 3 h / 100 °C
2.1: 391 g / hydroxylamine hydrochloride; pyridine / methanol / 1 h / Heating
3.1: 349 g / acetic anhydride / 3 h / 110 °C
4.1: 329 g / aq. nitric acid / acetic acid / 8 h / 45 - 50 °C
5.1: FeCl3; hydrazine hydrate / H2O; methanol / 3 h / Heating
5.2: 86 percent / HCl / H2O / 90 - 130 °C
View Scheme
Multi-step reaction with 6 steps
1.1: 88 percent / sodium formate; formic acid; hydroxylamine sulfate / 8 h / 85 °C
2.1: 95 percent / K2CO3 / dimethylformamide / 10 h / 85 °C
3.1: 95 percent / aq. H2SO4; HNO3; AcOH / 50 h / 20 °C
4.1: 75 percent / sodium dithionite / H2O / 20 - 50 °C
5.1: 38 percent / KOH / 2-methyl-butan-2-ol / 82 °C
6.1: formamide / 20 - 100 °C
6.2: 78 percent / 7 h / 100 °C
View Scheme
Multi-step reaction with 4 steps
1.1: formic acid; dihydrogen peroxide / 0 - 4 °C
1.2: Reflux
2.1: sodium carbonate / N,N-dimethyl-formamide / 10 h / 85 °C
3.1: trimethylaluminum / hexane; dichloromethane / 5 h / 0 °C / Inert atmosphere; Reflux
4.1: trichlorophosphate / toluene / 2 h / Reflux
View Scheme
4-methoxy-3-[3-(4-morpholinyl)propoxy]benzaldoxime
934191-95-4

4-methoxy-3-[3-(4-morpholinyl)propoxy]benzaldoxime

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 349 g / acetic anhydride / 3 h / 110 °C
2.1: 329 g / aq. nitric acid / acetic acid / 8 h / 45 - 50 °C
3.1: FeCl3; hydrazine hydrate / H2O; methanol / 3 h / Heating
3.2: 86 percent / HCl / H2O / 90 - 130 °C
View Scheme
4-methoxy-3-[3-(4-morpholinyl)propoxy]benzaldehyde
861453-11-4

4-methoxy-3-[3-(4-morpholinyl)propoxy]benzaldehyde

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 391 g / hydroxylamine hydrochloride; pyridine / methanol / 1 h / Heating
2.1: 349 g / acetic anhydride / 3 h / 110 °C
3.1: 329 g / aq. nitric acid / acetic acid / 8 h / 45 - 50 °C
4.1: FeCl3; hydrazine hydrate / H2O; methanol / 3 h / Heating
4.2: 86 percent / HCl / H2O / 90 - 130 °C
View Scheme
2-amino-4-methoxy-5-[(3-morpholin-4-yl)propoxy]benzonitrile
675126-27-9

2-amino-4-methoxy-5-[(3-morpholin-4-yl)propoxy]benzonitrile

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 38 percent / KOH / 2-methyl-butan-2-ol / 82 °C
2.1: formamide / 20 - 100 °C
2.2: 78 percent / 7 h / 100 °C
View Scheme
2-nitro-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzonitrile
675126-26-8

2-nitro-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzonitrile

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 75 percent / sodium dithionite / H2O / 20 - 50 °C
2.1: 38 percent / KOH / 2-methyl-butan-2-ol / 82 °C
3.1: formamide / 20 - 100 °C
3.2: 78 percent / 7 h / 100 °C
View Scheme
Multi-step reaction with 3 steps
1: dihydrogen peroxide; potassium carbonate / dimethyl sulfoxide / 1.5 h / 50 °C
2: palladium on activated charcoal / ethyl acetate; dichloromethane / 1.8 h / Reflux
3: formamide / 8 h / 20 °C / Reflux
View Scheme
2-methoxy-5-cyanophenol
52805-46-6

2-methoxy-5-cyanophenol

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 95 percent / K2CO3 / dimethylformamide / 10 h / 85 °C
2.1: 95 percent / aq. H2SO4; HNO3; AcOH / 50 h / 20 °C
3.1: 75 percent / sodium dithionite / H2O / 20 - 50 °C
4.1: 38 percent / KOH / 2-methyl-butan-2-ol / 82 °C
5.1: formamide / 20 - 100 °C
5.2: 78 percent / 7 h / 100 °C
View Scheme
Multi-step reaction with 5 steps
1: potassium carbonate / N,N-dimethyl-formamide / 10 h / 85 °C
2: nitric acid; sulfuric acid; acetic acid / 37 h / 0 - 20 °C
3: dihydrogen peroxide; potassium carbonate / dimethyl sulfoxide / 1.5 h / 50 °C
4: palladium on activated charcoal / ethyl acetate; dichloromethane / 1.8 h / Reflux
5: formamide / 8 h / 20 °C / Reflux
View Scheme
3-hydroxy-4-methoxybenzoate
6702-50-7

3-hydroxy-4-methoxybenzoate

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 76 percent / potassium carbonate / acetone / 24 h / Heating
2: 82 percent / nitric acid; trifluoroacetic acid / CH2Cl2 / 2 h / 20 °C
3: 60 percent / 1 h / 100 °C
4: hydrogen / palladium on activated carbon / methanol
5: 78 percent / 2-methoxy-ethanol / 2 h / 115 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium carbonate / N,N-dimethyl-formamide / 10 h / 85 °C
2: trimethylaluminum / hexane; dichloromethane / 5 h / 0 °C / Inert atmosphere; Reflux
3: trichlorophosphate / toluene / 2 h / Reflux
View Scheme
methyl 3-(3-chloropropoxy)-4-methoxybenzoate
380844-22-4

methyl 3-(3-chloropropoxy)-4-methoxybenzoate

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 82 percent / nitric acid; trifluoroacetic acid / CH2Cl2 / 2 h / 20 °C
2: 60 percent / 1 h / 100 °C
3: hydrogen / palladium on activated carbon / methanol
4: 78 percent / 2-methoxy-ethanol / 2 h / 115 °C
View Scheme
methyl 4-methoxy-5-(3-chloropropoxy)-2-nitrobenzoate
380844-24-6

methyl 4-methoxy-5-(3-chloropropoxy)-2-nitrobenzoate

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 60 percent / 1 h / 100 °C
2: hydrogen / palladium on activated carbon / methanol
3: 78 percent / 2-methoxy-ethanol / 2 h / 115 °C
View Scheme
4-methoxy-5-(3-morpholinylpropoxy)-2-nitrobenzoic acid methyl ester
214472-37-4

4-methoxy-5-(3-morpholinylpropoxy)-2-nitrobenzoic acid methyl ester

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogen / palladium on activated carbon / methanol
2: 78 percent / 2-methoxy-ethanol / 2 h / 115 °C
View Scheme
gefitinib
184475-35-2

gefitinib

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
With ammonia In hydrogenchloride
With ammonia In hydrogenchloride
Stage #1: gefitinib With hydrogenchloride In water for 6h; Heating / reflux;
Stage #2: With ammonia In water at 0℃;
Stage #1: gefitinib With hydrogenchloride In water for 6h; Heating / reflux;
Stage #2: With ammonium hydroxide In water
C16H14N2O2
1494468-50-6

C16H14N2O2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogen; palladium on activated charcoal
2: potassium carbonate / N,N-dimethyl-formamide
3: peracetic acid; sulfuric acid / ethanol / 12 h / 60 °C
View Scheme
6-hydroxy-7-methoxyquinazoline
884344-38-1

6-hydroxy-7-methoxyquinazoline

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide
2: peracetic acid; sulfuric acid / ethanol / 12 h / 60 °C
View Scheme
3-benzyloxy-4-methoxybenzaldehyde
6346-05-0

3-benzyloxy-4-methoxybenzaldehyde

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: nitric acid / water
2: hydrogenchloride; iron / ethanol
3: ethanol / Reflux
4: hydrogen; palladium on activated charcoal
5: potassium carbonate / N,N-dimethyl-formamide
6: peracetic acid; sulfuric acid / ethanol / 12 h / 60 °C
View Scheme
2-aldehyde-4-benzyloxy-5-methoxy nitrobenzene
58662-50-3

2-aldehyde-4-benzyloxy-5-methoxy nitrobenzene

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: hydrogenchloride; iron / ethanol
2: ethanol / Reflux
3: hydrogen; palladium on activated charcoal
4: potassium carbonate / N,N-dimethyl-formamide
5: peracetic acid; sulfuric acid / ethanol / 12 h / 60 °C
View Scheme
5-benzyloxy-4-methoxy-2-aminobenzaldehyde
1042978-66-4

5-benzyloxy-4-methoxy-2-aminobenzaldehyde

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: ethanol / Reflux
2: hydrogen; palladium on activated charcoal
3: potassium carbonate / N,N-dimethyl-formamide
4: peracetic acid; sulfuric acid / ethanol / 12 h / 60 °C
View Scheme
7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

4-chloro-7-methoxy-6-(3-morpholinopropoxy)quinazoline
199327-59-8

4-chloro-7-methoxy-6-(3-morpholinopropoxy)quinazoline

Conditions
ConditionsYield
With thionyl chloride; N,N-dimethyl-formamide for 4h; Heating;99.3%
With thionyl chloride In N,N-dimethyl-formamide at 84℃; for 1.5h;96.85%
With thionyl chloride; N,N-dimethyl-formamide at 84℃;94%
7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

6-acetoxy-4-chloro-7-methoxyquinazoline
230955-75-6

6-acetoxy-4-chloro-7-methoxyquinazoline

Conditions
ConditionsYield
With sulfuryl dichloride In acetonitrile at 55℃; Temperature; Concentration;93.7%
7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

4-(3-(4-chloro-7-methoxyquinazolin-6-yloxy)propyl)morpholine hydrochloride
1383952-42-8

4-(3-(4-chloro-7-methoxyquinazolin-6-yloxy)propyl)morpholine hydrochloride

Conditions
ConditionsYield
With triethylamine; trichlorophosphate In acetonitrile at 80 - 90℃; for 1h; Temperature; Reagent/catalyst; Solvent;84.1%
7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

3-chloro-4-fluorophenylamine
367-21-5

3-chloro-4-fluorophenylamine

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
Stage #1: 7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one With thionyl chloride; N,N-dimethyl-formamide for 1h; Reflux;
Stage #2: 3-chloro-4-fluorophenylamine In isopropyl alcohol for 1h; Reflux;		84%
With potassium carbonate In isopropyl alcohol at 80 - 85℃; for 1h;82%
Stage #1: 7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one With thionyl chloride In N,N-dimethyl-formamide for 2h; Heating;
Stage #2: 3-chloro-4-fluorophenylamine In N,N-dimethyl-formamide at 100℃; for 1h; Further stages.;		73%
Stage #1: 7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one With triethylamine; trichlorophosphate In toluene at 5 - 70℃;
Stage #2: 3-chloro-4-fluorophenylamine In isopropyl alcohol; toluene at 70℃; for 1h;		62.86%
Stage #1: 7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one With thionyl chloride for 4h; Reflux;
Stage #2: 3-chloro-4-fluorophenylamine In i-Amyl alcohol for 6h; Reflux;
7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

propargyl bromide
106-96-7

propargyl bromide

7-methoxy-6-[3-(morpholin-4-yl)propoxy]-3-(prop-2-yn-1-yl)quinazolin-4(3H)-one

7-methoxy-6-[3-(morpholin-4-yl)propoxy]-3-(prop-2-yn-1-yl)quinazolin-4(3H)-one

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;54%
7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

2-fluoroethyl tosylate
383-50-6

2-fluoroethyl tosylate

4-(3-((4-(2-fluoroethoxy)-7-methoxyquinazolin-6-yl)oxy)propyl)-morpholine

4-(3-((4-(2-fluoroethoxy)-7-methoxyquinazolin-6-yl)oxy)propyl)-morpholine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 90 - 100℃; for 2h;27%
7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

7-methoxy-6-[3-(4-morpholinyl)propoxy]quinazolin-4(3H)-thione
958669-54-0

7-methoxy-6-[3-(4-morpholinyl)propoxy]quinazolin-4(3H)-thione

Conditions
ConditionsYield
With tetraphosphorus decasulfide In pyridine for 24h; Heating;
7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

4-(methylthio)-7-methoxy-6-[3-(4-morpholinyl)propoxy]quinazoline
958669-55-1

4-(methylthio)-7-methoxy-6-[3-(4-morpholinyl)propoxy]quinazoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: P2S5 / pyridine / 24 h / Heating
2.1: aq. NaOH / methanol / 15 - 20 °C
2.2: 8.3 g / methanol; H2O / 5 h / 20 °C
View Scheme
7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: P2S5 / pyridine / 24 h / Heating
2.1: aq. NaOH / methanol / 15 - 20 °C
2.2: 8.3 g / methanol; H2O / 5 h / 20 °C
3.1: 85 percent / 3-chloro-4-fluoroaniline hydrochloride / propan-2-ol / 24 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 90 percent / POCl3; triethylamine / toluene / 24 h / 58 °C
2: 91 percent / triethylamine / propan-2-ol / 288 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: oxalyl chloride / CHCl3; dimethylformamide / Heating
2: 70 percent / dimethylformamide / 1 h / 145 °C
View Scheme
Multi-step reaction with 3 steps
1: trichlorophosphate / dichloromethane; N,N-dimethyl-formamide; acetonitrile / 3 h / 40 - 45 °C
2: hydrogenchloride / methanol; water / 1 h / 20 °C
3: sodium hydroxide / water / 1.5 h / 30 - 70 °C / pH 11 - 13
View Scheme
7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

O-Demethyl-Gefitinib
847949-49-9

O-Demethyl-Gefitinib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 90 percent / POCl3; triethylamine / toluene / 24 h / 58 °C
2: 91 percent / triethylamine / propan-2-ol / 288 h / Heating
3: 54 percent / LiCl / dimethylformamide / 15 h / Heating
View Scheme

7-Methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4(3H)-one Chemical Properties

Molecular structure of 7-Methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4(3H)-one (CAS NO.199327-61-2) is:

Product Name: 7-Methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4(3H)-one 
Empirical Formula: C16H21N3O4
Molecular Weight: 319.3556
CAS Registry Number: 199327-61-2
Index of Refraction: 1.611
Molar Refractivity: 83.535 cm3
Molar Volume: 240.745 cm3
Surface Tension: 49.021 dyne/cm
Density: 1.327 g/cm3
Flash Point: 268.002 °C
Enthalpy of Vaporization: 79.231 kJ/mol
Boiling Point: 519.53 °C at 760 mmHg
Product Categories: Heterocycles; Intermediates; Intermediates & Fine Chemicals; Pharmaceuticals

7-Methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4(3H)-one Uses

 7-Methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4(3H)-one (CAS NO.199327-61-2) can be used as Gefitinib intermediate.

7-Methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4(3H)-one Specification

 7-Methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4(3H)-one , its cas register number is 199327-61-2. It also can be called 7-methoxy-6-[3-(morpholin-4-yl)propoxy]quinazolin-4(1H)-one ; 7-Methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one ; 7-Methoxy-6-[3-(4-morpholinyl)propoxy]-4(3H)-quinazolinone .

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