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

HRID 964578Notes

Reaction equation

[NH2:1][C:2]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[CH:16][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1)=O.[CH3:24][O:25][C:26](=[O:30])[CH2:27][C:28]#[N:29].[Cl-].[Al+3].[Cl-].[Cl-]>O>[CH3:24][O:25][C:26](=[O:30])[CH2:27][C:28]1[N:29]=[C:4]([C:6]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=2)[C:3]2[C:2](=[CH:19][C:18]([O:20][CH3:21])=[C:17]([O:22][CH3:23])[CH:16]=2)[N:1]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 2-amino-4,5,3',4'-tetramethoxybenzophenone (6.3 g) and cyanoacetic acid methyl ester (23 ml), powdered aluminum chloride (5.3 g) was added, followed by stirring at 100° C. for 2.5 hours. The reaction mixture was poured over water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), after which the solvent was distilled off. The residue was subjected to silica gel column chromatography and eluted with hexane-ethyl acetate (4:1, v/v) to yield 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinazoline-2-acetic acid methyl ester (4.4 g, 55%), which was then recrystallized from isopropyl ether to yield a colorless needle crystal having a melting point of 152° to 153° C.

Workup

additionwas added
extractionextracted with ethyl acetate
washThe ethyl acetate layer was washed with water
dry with materialdried (MgSO4)
distillationafter which the solvent was distilled off
washeluted with hexane-ethyl acetate (4:1

Sources & evidence

ORD record: ord-eb3e83d824f44574b8d1dedecee924e6
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05770602

Reaction notes

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