6,7-Dimethoxy-3,4-dihydroquinazoline-4-one supplier

Name
6,7-Dimethoxy-3,4-dihydroquinazoline-4-one
EINECS 635-063-9
CAS No. 13794-72-4
Article Data137
CAS DataBase
Density 1.33 g/cm³
Solubility
Melting Point 309-311 °C
Formula C₁₀H₁₀N₂O₃
Boiling Point 374.1 °C at 760 mmHg
Molecular Weight 206.201
Flash Point 180.1 °C
Transport Information
Appearance White to off-white crystalline powder
Safety 26-37/39
Risk Codes 20/21/22-36/37/38
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms 4(1H)-Quinazolinone,6,7-dimethoxy- (9CI);6,7-Dimethoxy-4(3H)-quinazolinone;6,7-Dimethoxy-4-quinazolone;6,7-Dimethoxyquinazoline-4(3H)-one;6,7-Dimethoxyquinazoline-4-one;6,7-Dimethoxy-1H-quinazolin-4-one;
PSA 64.21000
LogP 0.94030

Synthetic route

: 26759-46-6
methyl 2-amino-4,5-dimethoxybenzoate

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

Conditions

Conditions	Yield
With sodium methylate; formamide In methanol; N,N-dimethyl-formamide for 10h; Heating;	97%

: 3473-63-0
formamidine acetic acid

: 5653-40-7
2-Amino-4,5-dimethoxybenzoic acid

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

Conditions

Conditions	Yield
In dimethyl sulfoxide at 140 - 170℃;	95.7%
In 2-methoxy-ethanol at 125℃; for 8h;	89.5%
Stage #1: formamidine acetic acid; 2-Amino-4,5-dimethoxybenzoic acid In ethyl methyl ether Reflux; Stage #2: With ammonium hydroxide In water	89%

: 20323-74-4
2-carboethoxy-4,5-dimethoxyaniline

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

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

Conditions

Conditions	Yield
at 165 - 170℃;	95%
at 168 - 170℃; Inert atmosphere;	89%
at 165 - 170℃; for 6h; Inert atmosphere;	73.2%

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

: 5653-40-7
2-Amino-4,5-dimethoxybenzoic acid

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

Conditions

Conditions	Yield
at 110 - 115℃; for 3h;	94.45%
at 140 - 145℃; for 4h;	93%
at 150℃;	89%

: 26759-46-6
methyl 2-amino-4,5-dimethoxybenzoate

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

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

Conditions

Conditions	Yield
With ammonia; acetic acid at 150℃; for 2h; Product distribution / selectivity;	93%
With ammonium acetate at 150℃; for 2h; Product distribution / selectivity;	92.1%
With formic acid at 145℃; for 18h;	91%

: 16712-16-6, 64165-14-6, 65387-22-6, 70179-79-2, 540-69-2
ammonium formate

: 5653-40-7
2-Amino-4,5-dimethoxybenzoic acid

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

Conditions

Conditions	Yield
With trimethyl orthoformate In methanol at 70℃; for 4h; Reflux;	93%
With trimethyl orthoformate In methanol at 70℃; for 4h;	93%

: 13790-39-1
6,7-dimethoxy-4-chloroquinazoline

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

Conditions

Conditions	Yield
With potassium hydroxide In tetrahydrofuran; water at 75℃; for 24h;	91%

: 5653-40-7
2-Amino-4,5-dimethoxybenzoic acid

: 463-52-5
formamidine

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

Conditions

Conditions	Yield
In 2-methoxy-ethanol at 100℃;	88%

: 4101-33-1
6,7-dimethoxy-N,N-quinazoline

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

Conditions

Conditions	Yield
With ammonium cerium (IV) nitrate; acetic acid In water	86%
With peracetic acid; sulfuric acid In ethanol at 60℃; for 4h; Solvent; Reagent/catalyst;	83%
With ammonium cerium (IV) nitrate; acetic acid In water at 20℃; for 0.0833333h;

: 67-56-1
methanol

: 5004-88-6
4,5-dimethoxyanthranilamide

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

Conditions

Conditions	Yield
With [Cp*Ir(2,2′-bpyO)(H2O)]; caesium carbonate at 130℃; for 2h; Microwave irradiation; Green chemistry;	86%
With [Cp*Ir(2,2'-bpyO)(H2O)]; caesium carbonate at 130℃; for 2h; Inert atmosphere; Microwave irradiation;	86%
With oxygen; copper(II) acetate monohydrate; caesium carbonate at 110℃; for 6h;	49%

: 128823-83-6
methyl 2-amino-5,6-dimethoxybenzoate

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

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

Conditions

Conditions	Yield
With ammonium formate at 170℃; for 12h;	86%

: 64-18-6
formic acid

: 102714-71-6
2-nitro-4,5-dimethoxybenzonitrile

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

Conditions

Conditions	Yield
Stage #1: 4,5-dimethoxy-2-nitrobenzonitrile With iron(III) chloride; hydrazine hydrate In methanol; water for 3h; Heating; Stage #2: formic acid With hydrogenchloride In water at 130℃; for 3h; Further stages.;	85%

: 5653-40-7
2-Amino-4,5-dimethoxybenzoic acid

: 149-73-5
trimethyl orthoformate

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

Conditions

Conditions	Yield
With ammonium acetate In methanol at 120℃; for 3h;	85%

: 26759-46-6
methyl 2-amino-4,5-dimethoxybenzoate

: 16712-16-6, 64165-14-6, 65387-22-6, 70179-79-2, 540-69-2
ammonium formate

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

Conditions

Conditions	Yield
In formamide at 190 - 200℃; for 2h;	84.7%
In formamide at 140℃; for 24h;

: 64-18-6
formic acid

: 26759-46-6
methyl 2-amino-4,5-dimethoxybenzoate

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

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

Conditions

Conditions	Yield
at 160℃; for 10h;	84.22%

...Expand

: 67-56-1
methanol

: 26961-27-3
2-amino-4,5-dimethoxybenzonitrile

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

Conditions

Conditions	Yield
With cobalt(II) nitrate hexahydrate; tris(2-diphenylphosphinoethyl)phosphine; water; caesium carbonate at 150℃; for 26h; Inert atmosphere; Sealed tube;	84%

: 6313-33-3
formamidine hydrochloride

: 5653-40-7
2-Amino-4,5-dimethoxybenzoic acid

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

Conditions

Conditions	Yield
at 210℃; for 0.25h;	79%
at 80 - 200℃;	65%
Stage #1: formamidine hydrochloride; 2-Amino-4,5-dimethoxybenzoic acid at 210℃; for 0.25h; Heating / reflux; Stage #2: With sodium hydroxide In water at 80℃;	64%
Stage #1: formamidine hydrochloride; 2-Amino-4,5-dimethoxybenzoic acid at 210℃; for 0.5h; Stage #2: With sodium hydroxide In water	64%
at 210℃; for 0.5h;	64%

: 5004-88-6
4,5-dimethoxyanthranilamide

: 67-68-5
dimethyl sulfoxide

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; dipotassium peroxodisulfate at 160℃; for 2h; Microwave irradiation;	62%

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

: C28H34N2O10

A: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

B: C28H32N4O6

Conditions

Conditions	Yield
at 186℃;	A 12.5% B 50%

...Expand

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

: C27H32N2O10

A: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

: C27H30N4O6

Conditions

Conditions	Yield
at 180 - 185℃; for 2h;	A 11.4% B 46.5%

...Expand

: 5653-40-7
2-Amino-4,5-dimethoxybenzoic acid

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

Conditions

Conditions	Yield
With formamide In water	18%
Multi-step reaction with 2 steps 1: 81.6 percent / Et3N / dioxane / 2 h / 20 °C 2: 12.5 percent / 186 °C View Scheme
Multi-step reaction with 2 steps 1: 76.8 percent / Et3N / dioxane / 3 h / 20 °C 2: 11.4 percent / 2 h / 180 - 185 °C View Scheme

: 290-87-9
1,3,5-Triazine

: 5653-40-7
2-Amino-4,5-dimethoxybenzoic acid

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

Conditions

Conditions	Yield
With piperidine In ethanol Cyclization;

: 5004-88-6
4,5-dimethoxyanthranilamide

: 149-73-5
trimethyl orthoformate

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

Conditions

Conditions	Yield
With hydrogenchloride

: 64-18-6
formic acid

: 5004-88-6
4,5-dimethoxyanthranilamide

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

Conditions

Conditions	Yield
for 5h; Heating;	1.18 g
Heating;

: 2024-83-1
veratronitrile

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 94 percent / aq. nitric acid / 1 h / 35 °C 2.1: FeCl3; hydrazine hydrate / H2O; methanol / 3 h / Heating 2.2: 85 percent / HCl / H2O / 3 h / 130 °C View Scheme

: 4998-07-6
4,5-dimethoxy-2-nitro-benzoic acid

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: SOCl2 2: NH4OH 3: NaBH4 / CuSO4 4: Heating View Scheme
Multi-step reaction with 4 steps 1: SOCl2 2: aq. NH3 3: CuSO4; NaBH4 4: Heating View Scheme
Multi-step reaction with 3 steps 1.1: thionyl chloride / 0.83 h / Heating 1.2: 88.5 percent / NH4OH 2.1: NaBH4; CuSO4 / methanol / 4 h 3.1: 1.18 g / 5 h / Heating View Scheme

: 4959-60-8
4,5-dimethoxy-2-nitrobenzamide

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaBH4 / CuSO4 2: Heating View Scheme
Multi-step reaction with 2 steps 1: CuSO4; NaBH4 2: Heating View Scheme
Multi-step reaction with 2 steps 1: NaBH4; CuSO4 / methanol / 4 h 2: 1.18 g / 5 h / Heating View Scheme

: 29568-78-3
4,5-dimethoxy-2-nitrobenzoyl chloride

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: NH4OH 2: NaBH4 / CuSO4 3: Heating View Scheme
Multi-step reaction with 3 steps 1: aq. NH3 2: CuSO4; NaBH4 3: Heating View Scheme

: 5004-88-6
4,5-dimethoxyanthranilamide

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

Conditions

Conditions	Yield
With formic acid Heating / reflux;

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

: 179688-52-9
6-hydroxy-7-methoxyquinazolin-4(3H)-one

Conditions

Conditions	Yield
With methanesulfonic acid; DL-methionine at 120℃; for 30h;	100%
With methanesulfonic acid; L-methionine at 100℃; for 22h;	94%
With methanesulfonic acid; L-methionine at 100℃; for 22h;	94%

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

: 16064-15-6
6,7-dihydroxy-3H-quinazolin-4-one

Conditions

Conditions	Yield
With hydrogen bromide In water at 135℃; for 18.5h;	100%
Stage #1: 3H-6,7-dimethoxyquinazolin-4-one With hydrogen bromide In water at 110℃; Reflux; Stage #2: With ammonia In water pH=7.0 - 7.5;	98.62%
With hydrogen bromide at 120℃;	97%

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

: 13790-39-1
6,7-dimethoxy-4-chloroquinazoline

Conditions

Conditions	Yield
With thionyl chloride In N,N-dimethyl-formamide for 6h; Heating / reflux;	98%
With thionyl chloride; N,N-dimethyl-formamide for 6h; Heating / reflux;	98%
In N-methyl-acetamide; thionyl chloride; dichloromethane	98%

L-Methionone: L-Methionone

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

: 179688-52-9
6-hydroxy-7-methoxyquinazolin-4(3H)-one

Conditions

Conditions	Yield
In methanesulfonic acid; water	97%

: 624-70-4
1-chloro-2-iodoethane

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

: 1609073-07-5
3-(2-chloroethyl)-6,7-dimethoxyquinazolin-4(3H)-one

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 50℃; Inert atmosphere;	96%
In N,N-dimethyl-formamide at 50℃;	96%

: 160879-62-9
methyl 1-phenylprop-2-enyl carbonate

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

: 6,7-dimethoxy-3-((S)-1-phenylallyl)quinazolin-4(3H)-one

Conditions

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-(+)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis[bis(3,5-di-tert-butylphenyl)phosphine] In 1,2-dichloro-ethane at 80℃; for 24h; Schlenk technique; Inert atmosphere; enantioselective reaction;	92%

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

: 1260640-98-9
4-bromo-6,7-dimethoxyquinazoline

Conditions

Conditions	Yield
With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 20℃; for 2h;	90.35%

: 108-24-7
acetic anhydride

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

: 179688-53-0
6-acetoxy-7-methoxy-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
Stage #1: 3H-6,7-dimethoxyquinazolin-4-one With methanesulfonic acid; DL-methionine at 120℃; for 24h; Stage #2: acetic anhydride With pyridine at 100℃; for 22h;	87%
With methanesulfonic acid; DL-methionine 1.) 100 deg C, 3 h, 2.) Py; Multistep reaction;

: 2969-81-5
4-bromoethylbutanoate

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

: 4-(6,7-dimethoxy-4-oxo-4H-quinazolin-3-yl)-butyric acid ethyl ester

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 10h; Alkylation;	87%

: 539-74-2
Ethyl 3-bromopropionate

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

: 3-(6,7-dimethoxy-4-oxo-4H-quinazolin-3-yl)-propionic acid ethyl ester

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 10h; Alkylation;	82%

: 2-((1-(tert-butoxycarbonyl)piperidin-4-yl)oxy)-2-oxoacetic acid

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

: tert-butyl 4-(6,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)-piperidine-1-carboxylate

Conditions

Conditions	Yield
With ammonium peroxydisulfate In water; dimethyl sulfoxide at 50℃; for 24h; Minisci Aromatic Substitution; Sealed tube;	82%

: 821-06-7
(E)-1,4-dibromobutene

: 13794-72-4
3H-6,7-dimethoxyquinazolin-4-one

: (E)-3-(4-bromobut-2-en-1-yl)-6,7-dimethoxyquinazolin-4(3H)-one

Conditions

Conditions	Yield
Stage #1: 3H-6,7-dimethoxyquinazolin-4-one With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: (E)-1,4-dibromobutene In N,N-dimethyl-formamide at 20℃; for 2h;	81%

6,7-Dimethoxy-3,4-dihydroquinazoline-4-one Chemical Properties

IUPAC Name: 6,7-Dimethoxy-1H-quinazolin-4-one
Synonyms of 6,7-Dimethoxy-3,4-dihydroquinazoline-4-one (CAS NO.13794-72-4): 6,7-Dimethoxy-1H-quinazolin-4-one ; 6,7-Dimethoxy-4(3H)-quinazolinone ; 4(1H)-Quinazolinone,6,7-dimethoxy- (9CI)
CAS NO: 13794-72-4
Molecular Formula: C₁₀H₁₀N₂O₃
Molecular Weight: 206.20
Molecular Structure:
H bond acceptors: 5
H bond donors: 1
Freely Rotating Bonds: 2
Polar Surface Area: 51.13 Å²
Index of Refraction: 1.6
Molar Refractivity: 52.89 cm³
Molar Volume: 154.5 cm³
Surface Tension: 44.6 dyne/cm
Density: 1.33 g/cm³
Flash Point: 180.1°C
Melting point: 309-311°C
Enthalpy of Vaporization: 62.15 kJ/mol
Boiling Point: 374.1 °C at 760 mmHg
Vapour Pressure: 8.53E-06 mmHg at 25°C
SMILES: O=C2\N=C/Nc1cc(OC)c(OC)cc12
InChI: InChI=1/C10H10N2O3/c1-14-8-3-6-7(4-9(8)15-2)11-5-12-10(6)13/h3-5H,1-2H3,(H,11,12,13)
InChIKey: DMSRMHGCZUXCMJ-UHFFFAOYAF
Std. InChI: InChI=1S/C10H10N2O3/c1-14-8-3-6-7(4-9(8)15-2)11-5-12-10(6)13/h3-5H,1-2H3,(H,11,12,13)
Std. InChIKey: DMSRMHGCZUXCMJ-UHFFFAOYSA-N
Product Categories of 6,7-Dimethoxy-3,4-dihydroquinazoline-4-one (CAS NO.13794-72-4): blocks;Heterocycles;Quinolines;pharmacetical;Tinibs;Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals

6,7-Dimethoxy-3,4-dihydroquinazoline-4-one Uses

6,7-Dimethoxy-3,4-dihydroquinazoline-4-one (CAS NO.13794-72-4) is used ad Gefitinib intermediate.

6,7-Dimethoxy-3,4-dihydroquinazoline-4-one Safety Profile

Safety Information about 6,7-Dimethoxy-3,4-dihydroquinazoline-4-one (CAS NO.13794-72-4):
Hazard Codes: Harmful Xn,Xi
Risk Statements: 20/21/22-36/37/38
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39: Wear suitable gloves and eye/face protection.
Hazard Note: Irritant
HazardClass: IRRITANT

Product Name

6,7-Dimethoxy-3,4-dihydroquinazoline-4-one

Synthetic route

6,7-Dimethoxy-3,4-dihydroquinazoline-4-one Chemical Properties

6,7-Dimethoxy-3,4-dihydroquinazoline-4-one Uses

6,7-Dimethoxy-3,4-dihydroquinazoline-4-one Safety Profile

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