Methyl cyanoacetate → 6,7-Dimethoxy-4-(3,4-dimethoxyphenyl)quinazoline-2-acetic acid methyl ester

HRID 266120Notes

Reaction equation

[Cl-].[Al+3].[Cl-].[Cl-].[NH2:5][C:6]1[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[CH:20][C:7]=1[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1)=O.[C:28]([CH2:30][C:31]([O:33][CH3:34])=[O:32])#[N:29]>O>[CH3:19][O:18][C:12]1[CH:11]=[C:10]([C:8]2[C:7]3[C:6](=[CH:23][C:22]([O:24][CH3:25])=[C:21]([O:26][CH3:27])[CH:20]=3)[N:5]=[C:28]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[N:29]=2)[CH:15]=[CH:14][C:13]=1[O:16][CH3:17]

Participants

Conditions

Temperature: 100 °C

Procedure

Aluminium chloride powder (5.3 g) was added to a mixture of 2-amino-4,5,3',4'-tetramethoxybenzophenone (6.3 g) and methyl cyanoacetate (23 ml), and the mixture was stirred at 100° C. for 2.5 hours. The reaction mixture was poured into water and extracted with chloroform. The chloroform layer was washed with water and dried over magnesium sulfate. The residue was subjected to column chromatography on silica gel. The fractions eluted with hexane-ethyl acetate (4:1, v/v) gave methyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinazoline-2-acetate. This compound was recrystallized from acetone. Colorless needles, mp. 152°-153° C.

Workup

extractionextracted with chloroform
washThe chloroform layer was washed with water
dry with materialdried over magnesium sulfate
washThe fractions eluted with hexane-ethyl acetate (4:1

Sources & evidence

ORD record: ord-41f7c6e978974dc5ae6e3a2c6dd0184f
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05650410

Reaction notes

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