Ethyl Propionate → methyl 3-(1-benzyl-4-methyl-1H-imidazol-2-yl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 907849Notes

Reaction equation

[CH2:1]([N:8]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]1[CH:14]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:16](=[N:23]/[C:24]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:25]=1[CH2:26][O:27][C:28]2=[O:33])\[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH3:34][O-:35].[Na+].C(OCC)(=O)CC>>[CH2:1]([N:8]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]1[CH:14]1[C:34](=[O:35])[C:25]2[C:29]([C:28]([O:27][CH3:26])=[O:33])=[CH:30][CH:31]=[CH:32][C:24]=2[NH:23][CH:16]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 4

HCID 7749Ethyl Propionate

HCID 10942334Sodium Methoxide

HCID 866390371-benzyl-4-methyl-1H-imidazole-2-carbaldehyde

HCID 178519069HCID 178519069, compound

Product 1

HCID 67260654methyl 3-(1-benzyl-4-methyl-1H-imidazol-2-yl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylateYield 25%

Procedure

A mixture of 1-benzyl-4-methyl-1H-imidazole-2-carbaldehyde (450 mg, 2.25 mmol), (E)-4-(benzylideneamino)isobenzofuran-1(3H)-one (640 mg, 2.7 mmol), sodium methanolate (207 mg, 9 mmol) and ethyl propionate (25 mL) were stirred at room temperature overnight. Then the resulting mixture was evaporated under reduced pressure and extracted with ethyl acetate (4×100 mL) and concentrated to give methyl 3-(1-benzyl-4-methyl-1H-imidazol-2-yl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate (250 mg, yield 25%). LC-MS (ESI) m/z: 438 (M+1)+.

Workup

customThen the resulting mixture was evaporated under reduced pressure
extractionextracted with ethyl acetate (4×100 mL)
concentrationconcentrated

Sources & evidence

ORD record: ord-286038318dc046d788906b1fc60f006c
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012976B2

Reaction notes

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