• Name

  6,7-Bis-(2-methoxyethoxy)-4(3H)-quinazolinone

• EINECS 605-867-4
• CAS No. 179688-29-0
• Article Data47
• CAS DataBase
• Density 1.26 g/cm³
• Solubility
• Melting Point 185-189 °C
• Formula C₁₄H₁₈N₂O₅
• Boiling Point 467.8 °C at 760 mmHg
• Molecular Weight 294.307
• Flash Point 236.7 °C
• Transport Information
• Appearance off-white solid
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms 6,7-bis-(2-Methoxyethoxy)quinazolin-4(3h)-one;4(1H)-Quinazolinone,6,7-bis(2-methoxyethoxy)- (9CI);6,7-Bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one;6,7-Bis(2-methoxyethoxy)quinazolin-4(3H)-one;6,7-Di(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one;4(3H)-Quinazolinone,6,7-bis(2-methoxyethoxy)-;
• PSA 82.67000
• LogP 0.97350

Synthetic route

C14H17NO6

179688-29-0

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
With ammonium hydroxide; tetrabutylammomium bromide for 0.0833333h; Time; Irradiation;	99.2%
With ammonium hydroxide; tetrabutylammomium bromide In dichloromethane at 20℃; Reagent/catalyst;	99.2%
With ammonium hydroxide; tetrabutylammomium bromide for 0.0833333h; Time; Sonication;	99.2%
With ammonium hydroxide; tetrabutyl ammonium fluoride at 20℃; for 0.25h; Time; Sonication;	99.2%

3473-63-0

formamidine acetic acid

179688-27-8

ethyl 2-amino-4,5-bis(2-methoxyethoxy)-benzoate

179688-29-0

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
Stage #1: formamidine acetic acid; ethyl 2-amino-4,5-bis(2-methoxyethoxy)-benzoate In butan-1-ol at 80℃; for 5h; Inert atmosphere; Stage #2: In Isopropyl acetate for 1h; Reflux;	98%
In ethanol at 55℃; for 3h; Concentration; Temperature; Solvent; Green chemistry;	98.5%
In 2-methoxy-ethanol at 125℃; for 8h;	63.5%

1208902-93-5

6,7-di(2'-methoxyethoxy)quinazoline

179688-29-0

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
With peracetic acid; sulfuric acid In ethanol at 60℃; for 4h;	93%
Stage #1: 6,7-di(2'-methoxyethoxy)quinazoline With ammonium cerium (IV) nitrate; acetic acid In water Stage #2: With sodium hydroxide In water	88%

107-31-3

Methyl formate

476168-17-9

2-amino-4,5-bis-(2-methoxyethoxy)-benzoic acid methyl ester

179688-29-0

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
With ammonia In methanol for 7h; Concentration; Reflux;	92%

50-00-0

formaldehyd

236750-62-2

2-amino-4,5-bis(2-methoxyethyloxy)benzamide

179688-29-0

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
In water at 130℃; for 24h; Temperature;	92%

119072-55-8, 7188-38-7

tert-butylisonitrile

236750-62-2

2-amino-4,5-bis(2-methoxyethyloxy)benzamide

179688-29-0

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
With chloro-trimethyl-silane In acetonitrile at 70℃;	92%

179688-27-8

ethyl 2-amino-4,5-bis(2-methoxyethoxy)-benzoate

179688-29-0

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
With ammonium formate In N,N-dimethyl-formamide at 160℃;	79%

2-((6,7-bis(2-methoxyethoxy))-4-quinazolinylamino)-ethanol

179688-29-0

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
With hydrogenchloride In water at 100 - 105℃; for 2h;	71%
With hydrogenchloride In water at 100 - 105℃; for 2h;

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

ammonium formate

179688-27-8

ethyl 2-amino-4,5-bis(2-methoxyethoxy)-benzoate

179688-29-0

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
In formamide at 160℃; for 3h;	62%

1006377-63-4

C13H19NO5

179688-29-0

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: acetic anhydride / 110 °C 2.1: 85 percent / aq. nitric acid / acetic acid / 8 h / 45 - 50 °C 3.1: FeCl3; hydrazine hydrate / H2O; methanol / 3 h / Heating 3.2: 81 percent / HCl / H2O / 90 - 130 °C View Scheme

80407-68-7

3,4-bis(2-methoxyethoxy) benzonitrile

179688-29-0

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 85 percent / aq. nitric acid / acetic acid / 8 h / 45 - 50 °C 2.1: FeCl3; hydrazine hydrate / H2O; methanol / 3 h / Heating 2.2: 81 percent / HCl / H2O / 90 - 130 °C View Scheme
Multi-step reaction with 4 steps 1: nitric acid 2: dihydrogen peroxide 3: palladium on activated charcoal; ammonium formate 4: water / 24 h / 130 °C View Scheme
Multi-step reaction with 3 steps 1.1: nitric acid / dichloromethane / 12 h / 20 °C 2.1: pyrographite; iron(III) chloride; hydrazine hydrate / methanol / 4 h / Reflux 2.2: 12 h / Reflux 3.1: methanol / 8 h / Reflux View Scheme

80407-64-3

3,4-bis(2-methoxyethoxy)benzaldehyde

179688-29-0

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hydroxylamine hydrochloride; pyridine / methanol / Heating 2.1: acetic anhydride / 110 °C 3.1: 85 percent / aq. nitric acid / acetic acid / 8 h / 45 - 50 °C 4.1: FeCl3; hydrazine hydrate / H2O; methanol / 3 h / Heating 4.2: 81 percent / HCl / H2O / 90 - 130 °C View Scheme
Multi-step reaction with 4 steps 1: nitric acid / water 2: hydrogenchloride; iron / ethanol 3: ethanol / Reflux 4: peracetic acid; sulfuric acid / ethanol / 4 h / 60 °C View Scheme
Multi-step reaction with 5 steps 1: potassium permanganate; sodium hydroxide / water / 14.42 h / 0 - 40 °C 2: sulfuric acid / 5 h / 0 - 10 °C 3: nitric acid; sulfuric acid / chloroform / 1.5 h / 0 - 40 °C 4: iron; ammonium chloride; hydrogenchloride / water; ethanol / 15 h / 80 °C / Inert atmosphere 5: ammonia / methanol / 7 h / Reflux View Scheme
Multi-step reaction with 5 steps 1: hydroxylamine hydrochloride; acetic anhydride 2: nitric acid 3: dihydrogen peroxide 4: palladium on activated charcoal; ammonium formate 5: water / 24 h / 130 °C View Scheme
Multi-step reaction with 4 steps 1.1: formic acid; hydroxylamine hydrochloride; sodium formate / 8 h / 90 - 100 °C 2.1: nitric acid / dichloromethane / 12 h / 20 °C 3.1: pyrographite; iron(III) chloride; hydrazine hydrate / methanol / 4 h / Reflux 3.2: 12 h / Reflux 4.1: methanol / 8 h / Reflux View Scheme

139-85-5

3,4-dihydroxybenzaldehyde

179688-29-0

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 98 percent / potassium carbonate / dimethylformamide / 100 °C 2.1: hydroxylamine hydrochloride; pyridine / methanol / Heating 3.1: acetic anhydride / 110 °C 4.1: 85 percent / aq. nitric acid / acetic acid / 8 h / 45 - 50 °C 5.1: FeCl3; hydrazine hydrate / H2O; methanol / 3 h / Heating 5.2: 81 percent / HCl / H2O / 90 - 130 °C View Scheme
Multi-step reaction with 6 steps 1: potassium carbonate; tetrabutylammomium bromide / N,N-dimethyl-formamide / 105 - 110 °C / Inert atmosphere 2: potassium permanganate; sodium hydroxide / water / 14.42 h / 0 - 40 °C 3: sulfuric acid / 5 h / 0 - 10 °C 4: nitric acid; sulfuric acid / chloroform / 1.5 h / 0 - 40 °C 5: iron; ammonium chloride; hydrogenchloride / water; ethanol / 15 h / 80 °C / Inert atmosphere 6: ammonia / methanol / 7 h / Reflux View Scheme
Multi-step reaction with 5 steps 1.1: sodium iodide / N,N-dimethyl-formamide / Reflux 2.1: formic acid; hydroxylamine hydrochloride; sodium formate / 8 h / 90 - 100 °C 3.1: nitric acid / dichloromethane / 12 h / 20 °C 4.1: pyrographite; iron(III) chloride; hydrazine hydrate / methanol / 4 h / Reflux 4.2: 12 h / Reflux 5.1: methanol / 8 h / Reflux View Scheme

3943-89-3

Ethyl protocatechuate

179688-29-0

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium carbonate; tetrabutylammonium iodide / acetone / 120 h / Heating 2: acetic acid; nitric acid / 24 h / 20 °C 3: hydrogen / PtO2*H2O / methanol / 20 °C / 2585.74 Torr 4: 84 percent / 12 h / 165 - 170 °C View Scheme
Multi-step reaction with 4 steps 1: potassium carbonate; tetrabutylammonium iodide / acetone 2: acetic acid; nitric acid / 24 h / 20 °C 3: hydrogen / PtO2*H2O / methanol / 20 °C / 2585.74 Torr 4: 84 percent / 12 h / 165 - 170 °C View Scheme
Multi-step reaction with 4 steps 1: 68 percent / potassium carbonate; tetrabutylammonium iodide / acetone / 72 h / Heating 2: nitric acid; trifluoroacetic acid / CH2Cl2 / 20 °C 3: 94 percent / hydrogen / palladium on activated carbon / methanol 4: 62 percent / formamide / 3 h / 160 °C View Scheme

183322-16-9

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

179688-29-0

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid; nitric acid / 24 h / 20 °C 2: hydrogen / PtO2*H2O / methanol / 20 °C / 2585.74 Torr 3: 84 percent / 12 h / 165 - 170 °C View Scheme
Multi-step reaction with 3 steps 1: nitric acid; trifluoroacetic acid / CH2Cl2 / 20 °C 2: 94 percent / hydrogen / palladium on activated carbon / methanol 3: 62 percent / formamide / 3 h / 160 °C View Scheme
Multi-step reaction with 3 steps 1: acetic acid; nitric acid / 0 °C 2: hydrogen; palladium on activated charcoal / methanol 3: 165 - 170 °C View Scheme

179688-26-7

2-nitro-4,5-bis(2-methoxyethoxy)benzoic acid ethyl ester

179688-29-0

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen / PtO2*H2O / methanol / 20 °C / 2585.74 Torr 2: 84 percent / 12 h / 165 - 170 °C View Scheme
Multi-step reaction with 2 steps 1: 94 percent / hydrogen / palladium on activated carbon / methanol 2: 62 percent / formamide / 3 h / 160 °C View Scheme
Multi-step reaction with 2 steps 1: hydrogen; palladium on activated charcoal / methanol 2: 165 - 170 °C View Scheme

3473-63-0

formamidine acetic acid

476168-17-9

2-amino-4,5-bis-(2-methoxyethoxy)-benzoic acid methyl ester

179688-29-0

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
In 2-methoxy-ethanol for 24h; Heating / reflux;
In ethanol Reflux;

54060-30-9

3-acetylenephenylamine

183322-18-1

4-chloro-6,7-bis(2-methoxyethoxy)quinazoline

A

179688-29-0

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

B

183319-69-9

erlotinib hydrochloride

Conditions

Conditions	Yield
Stage #1: 3-acetylenephenylamine; 4-chloro-6,7-bis(2-methoxyethoxy)quinazoline With pyridine In isopropyl alcohol at 80℃; for 1h; Stage #2: With hydrogenchloride In 1,4-dioxane; diethyl ether; chloroform at 20℃; for 1h; Product distribution / selectivity;
Stage #1: 3-acetylenephenylamine; 4-chloro-6,7-bis(2-methoxyethoxy)quinazoline With pyridine In isopropyl alcohol at 80℃; for 1h; Stage #2: With hydrogenchloride In 1,4-dioxane; diethyl ether; chloroform at 20℃;

...Expand

179688-14-3

methyl 3,4-bis{[2-(methyloxy)ethyl]oxy}benzoate

179688-29-0

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: nitric acid; acetic anhydride; acetic acid / acetic acid / 0 - 5 °C 2: hydrogen / ethanol 3: ethanol / Reflux View Scheme
Multi-step reaction with 3 steps 1: nitric acid; sulfuric acid / chloroform / 1.5 h / 0 - 40 °C 2: iron; ammonium chloride; hydrogenchloride / water; ethanol / 15 h / 80 °C / Inert atmosphere 3: ammonia / methanol / 7 h / Reflux View Scheme

501684-22-6

methyl 4,5-bis(2-methoxyethoxy)-2-nitrobenzoate

179688-29-0

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen / ethanol 2: ethanol / Reflux View Scheme

179688-29-0

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

183322-18-1

4-chloro-6,7-bis(2-methoxyethoxy)quinazoline

Conditions

Conditions	Yield
With oxalyl dichloride In chloroform; N,N-dimethyl-formamide for 1.5h; Heating;	98%
With oxalyl dichloride In dichloromethane Solvent; Reagent/catalyst; Temperature; Reflux; Large scale;	97%
With thionyl chloride In N,N-dimethyl-formamide at 60℃; Temperature; Concentration;	95.6%

179688-29-0

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

958669-56-2

6,7-bis(2-methoxyethoxy)quinazoline-4(3H)-thione

Conditions

Conditions	Yield
With pyridine; tetraphosphorus decasulfide for 15h; Reflux;	97%
With tetraphosphorus decasulfide In pyridine for 24h; Heating;	95%

179688-29-0

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

54060-30-9

3-acetylenephenylamine

183319-69-9

erlotinib hydrochloride

Conditions

Conditions	Yield
for 3h; Temperature; Reflux; Large scale;	95.1%

179688-29-0

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

67-56-1

methanol

1312937-41-9

6,7-bis(2-methoxyethoxy)-4-methoxyquinazoline

Conditions

Conditions	Yield
Stage #1: 6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one With trichlorophosphate; N,N-dimethyl-formamide at 80℃; for 0.5h; Stage #2: methanol With potassium carbonate In toluene at 0 - 40℃; for 0.5h; Product distribution / selectivity;	94%
Stage #1: 6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one With trichlorophosphate; N,N-dimethyl-formamide at 80℃; for 0.5h; Stage #2: methanol With potassium carbonate In N,N-dimethyl-formamide; toluene at 0 - 40℃; Product distribution / selectivity;	94%

6,7-Bis-(2-methoxyethoxy)-4(3H)-quinazolinone Chemical Properties

6,7-Bis-(2-methoxyethoxy)-4(3H)-quinazolinone Uses

6,7-Bis-(2-methoxyethoxy)-4(3H)-quinazolinone Specification