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

HRID 964572Notes

Reaction equation

HRID 964572 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.[C:24]([O:30][CH2:31][CH2:32][CH3:33])(=[O:29])[CH2:25][C:26]([CH3:28])=O.S(=O)(=O)(O)O>C(O)(=O)C>[CH2:31]([O:30][C:24]([C:25]1[C:26]([CH3:28])=[N:1][C:2]2[C:3]([C:4]=1[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1)=[CH:16][C:17]([O:22][CH3:23])=[C:18]([O:20][CH3:21])[CH:19]=2)=[O:29])[CH2:32][CH3:33]

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

To a mixture of 2-amino-4,5,3',4'-tetramethoxybenzophenone, propyl acetoacetate and acetic acid, concentratd sulfuric acid was added, followed by the same treatment as in Reference Example 1, to yield 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-methylquinoline-3-carboxylic acid propyl ester (79%), which was then recrystallized from ethyl acetate-isopropyl ether to yield a colorless prismatic crystal having a melting point of 153° to 155° C.

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-45fffd9f78b24604889745bed722db2a
Source dataset
uspto-grants-1998_06
Patent number
US05770602

Reaction notes

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