Hydrochloric Acid → 7-Benzyloxy-6-methoxy-3H-quinazolin-4-one

HRID 1375773Notes

Reaction equation

[NH2:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9]([O:20][CH3:21])=[CH:8][C:3]=1[C:4](OC)=[O:5].[CH:22]([NH2:24])=O.C[O-].[Na+].Cl>CN(C)C=O.CO.O>[CH2:13]([O:12][C:10]1[CH:11]=[C:2]2[C:3]([C:4](=[O:5])[NH:24][CH:22]=[N:1]2)=[CH:8][C:9]=1[O:20][CH3:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Methyl 2-amino-4-(benzyloxy)-5-methoxybenzoate (650 mg) was dissolved in N,N-dimethylformamide (15 ml) and methanol (3 ml). Formamide (0.46 ml) and sodium methoxide (373 mg) were added to the solution. The mixture was heated to 100° C. and was stirred overnight. The reaction solution was cooled to room temperature, and 10 ml of water was then added to the cooled reaction solution. The reaction solution was neutralized with a 1 M aqueous hydrochloric acid solution to precipitate a solid. The solid was collected by filtration, was washed with water and ether, and was then dried through a vacuum pump to give 566 mg (yield 87%) of the title compound.

Workup

temperatureThe reaction solution was cooled to room temperature
customto precipitate a solid
filtrationThe solid was collected by filtration
washwas washed with water and ether
customwas then dried through a vacuum pump

Sources & evidence

ORD record: ord-e36a2c05beb945eeaec539c80930746d
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07169789B2

Reaction notes

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