Dimethyl 3-oxoglutarate → HCID 22097612, compound

HRID 862629Notes

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]([CH2:28][C:29]([CH2:31][C:32]([O:34][CH3:35])=[O:33])=O)=[O:27]>S(=O)(=O)(O)O.C(O)(=O)C>[CH3:23][O:22][C:17]1[CH:16]=[C:3]2[C:2](=[CH:19][C:18]=1[O:20][CH3:21])[N:1]=[C:29]([CH2:28][C:26]([O:25][CH3:24])=[O:27])[C:31]([C:32]([O:34][CH3:35])=[O:33])=[C:4]2[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Three drops of conc. sulfuric acid was added to a mixture of 2-amino-4,5,3',4'-tetramethoxybenzophenone (1.55 g), dimethyl acetonedicarboxylate (0.936 g) and acetic acid (30 ml), and the resulting mixture was stirred at 100° C. for 2.5 hours. The reaction mixture was concentrated under reduced pressure, the residue was poured into water, neutralized with an aqueous saturated sodium bicarbonate solution and extracted with chloroform. The chloroform layer was washed with water dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting crystals were recrystallized from acetone to give methyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-3-methoxycarbonylquinoline-2-acetate (1.41 g, 64%). Colorless prisms. mp. 170°-171° C.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
additionthe residue was poured into water
extractionextracted with chloroform
washThe chloroform layer was washed with water
dry with materialdried over magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe resulting crystals were recrystallized from acetone

Sources & evidence

ORD record: ord-94997b27eadc4b9faf29b7f5a6759572
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05719157

Reaction notes

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