Sulfuric Acid → HCID 11799027, compound

HRID 266124

Reaction equation

S(=O)(=O)(O)O.[NH2:6][C:7]1[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[CH:21][C:8]=1[C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)=O.[CH3:29][CH2:30][O:31][C:32]([CH2:34][C:35]([CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])=O)=[O:33]>C(O)(=O)C>[CH3:20][O:19][C:13]1[CH:12]=[C:11]([C:9]2[C:8]3[C:7](=[CH:24][C:23]([O:25][CH3:26])=[C:22]([O:27][CH3:28])[CH:21]=3)[N:6]=[C:35]([CH2:34][C:32]([O:31][CH2:30][CH3:29])=[O:33])[C:37]=2[C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:16]=[CH:15][C:14]=1[O:17][CH3:18]

Participants

Conditions

Temperature: 100 °C

Procedure

Conc. sulfuric acid (1.5 ml) was added to a mixture of 2-amino-4,5,3',4'-tetramethoxybenzophenone (50.0 g), diethyl acetonedicarboxylate (35.0 g) and acetic acid (400 ml), and the 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 solution of sodium bicarbonate, and extracted with chloroform. The chloroform layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residual crystals were recrystallized from acetone to give ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-3-ethoxycarbonylquinoline-2-acetate (48.8 g, 64%). Colorless prisms, mp. 146°-147° 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 residual crystals were recrystallized from acetone

Sources & evidence

ORD record: ord-ef881ca9d2034a3ba0e5b9106fd38325
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05650410

Linked notes

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