Sulfuric Acid → 6,7-Dimethoxy-4-(3,4-dimethoxyphenyl)-2-methylquinoline-3-carboxylic acid propyl ester

HRID 266117Notes

Reaction equation

HRID 266117 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.[CH2:29]([O:32][C:33](=[O:38])[CH2:34][C:35]([CH3:37])=O)[CH2:30][CH3:31]>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]([CH3:37])[C:34]=2[C:33]([O:32][CH2:29][CH2:30][CH3:31])=[O:38])[CH:16]=[CH:15][C:14]=1[O:17][CH3:18]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 74507Propyl acetoacetateHCID 99269672-Amino-4,5,3',4'-tetramethoxybenzophenone

Product 1

HCID 218511596,7-Dimethoxy-4-(3,4-dimethoxyphenyl)-2-methylquinoline-3-carboxylic acid propyl esterYield 79%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Conc. sulfuric acid was added to a mixture of 2-amino-4,5,3',4'-tetramethoxybenzophenone, propylacetoacetate and acetic acid. The mixture was treated according to the same manner as in Reference Example 1 to give propyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-methylquinoline-3-carboxylate (79%). This compound was recrystallized from ethyl acetateisopropyl ether. Colorless prisms, mp. 153°-155° C.

Workup

  1. additionThe mixture was treated

Sources & evidence

ORD record
ord-1433fbcf21f1494ba7871cc79d09194a
Source dataset
uspto-grants-1997_07
Patent number
US05650410

Reaction notes

Loading…