Sulfuric Acid → Ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate

HRID 1940169Notes

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.[Cl:24][CH2:25][C:26](=O)[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].S(=O)(=O)(O)O>C(O)(=O)C>[Cl:24][CH2:25][C:26]1[C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:4]([C:6]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=2)[C:3]2[C:2](=[CH:19][C:18]([O:20][CH3:21])=[C:17]([O:22][CH3:23])[CH:16]=2)[N:1]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 2-amino-3',4,4',5-tetramethoxybenzophenone (6.6 g), ethyl 4-chloroacetoacetate (3.7 g) and acetic acid (60 ml) was added concentrated sulfuric acid (0.3 ml) and the mixture was stirred at 100° C. for 3 hours. The reaction mixture was then concentrated under reduced pressure and the residue was poured in water, made basic with 2N--NaOH, and extracted with chloroform. The chloroform layer was washed with water and dried (MgSO4) and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with chloroform-ethyl acetate (7:3, v/v) to give ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate (53%). Recrystallization from acetone-ether provided colorless prisms, m.p. 147°-148° C.

Workup

concentrationThe reaction mixture was then concentrated under reduced pressure
additionthe residue was poured in water
extractionNaOH, and extracted with chloroform
washThe chloroform layer was washed with water
dry with materialdried (MgSO4)
distillationthe solvent was distilled off under reduced pressure
washeluted with chloroform-ethyl acetate (7:3

Sources & evidence

ORD record: ord-7645058c5bf34305939cffeeaa5a7797
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05698699

Reaction notes

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