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

HRID 617211Notes

Reaction equation

HRID 617211 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.[C:29]([O:35][CH2:36][CH2:37][CH3:38])(=[O:34])[CH2:30][C:31]([CH3:33])=O>C(O)(=O)C>[CH3:28][O:27][C:22]1[CH:21]=[C:8]2[C:7](=[CH:24][C:23]=1[O:25][CH3:26])[N:6]=[C:31]([CH3:33])[C:30]([C:29]([O:35][CH2:36][CH2:37][CH3:38])=[O:34])=[C:9]2[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1

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, propyl acetoacetate and acetic acid. The resulting mixture was treated according to the same manner as that described in Reference example 1 to obtain propyl 6,7-dimethoxy-4-(3,4- dimethoxyphenyl)-2-methylquinoline-3-carboxylate (79%) which was recrystallized from ethyl acetate/isopropyl ether.

Workup

  1. additionThe resulting mixture was treated

Sources & evidence

ORD record
ord-5af6e7af5c5149a899c8f1faae6e54af
Source dataset
uspto-grants-1999_09
Patent number
US05948782

Reaction notes

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