Sulfuric Acid → Ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-methylquinoline-3-carboxylate

HRID 266115Notes

Reaction equation

HRID 266115 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][CH3:37])(=[O:34])[CH2:30][C:31]([CH3:33])=O>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:31]([CH3:33])[C:30]=2[C:29]([O:35][CH2:36][CH3:37])=[O:34])[CH:16]=[CH:15][C:14]=1[O:17][CH3:18]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8868Ethyl AcetoacetateHCID 99269672-Amino-4,5,3',4'-tetramethoxybenzophenone

Product 1

HCID 19032371Ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-methylquinoline-3-carboxylateYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Conc. sulfuric acid was added to a mixture of 2-amino-4,5,3',4'-tetramethoxybenzophenone, ethyl acetoacetate and acetic acid. The mixture was treated according to the same manner as in Reference Example 1 to give ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-methylquinoline-3-carboxylate (83%). This compound was recrystallized from ethanol. Colorless prisms, mp. 147°-148° C.

Workup

  1. additionThe mixture was treated

Sources & evidence

ORD record
ord-04165f1360b945ea8d0c598e9f87f189
Source dataset
uspto-grants-1997_07
Patent number
US05650410

Reaction notes

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