Phosphorus tribromide → Ethyl 2-(2-bromoethyl)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate

HRID 1458922Notes

Reaction equation

P(Br)(Br)[Br:2].O[CH2:6][CH2:7][C:8]1[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:16]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=2)[C:15]2[C:10](=[CH:11][C:12]([O:35][CH3:36])=[C:13]([O:33][CH3:34])[CH:14]=2)[N:9]=1.C(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[Br:2][CH2:6][CH2:7][C:8]1[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:16]([C:15]2[CH:10]=[CH:11][C:12]([O:35][CH3:36])=[C:13]([O:33][CH3:34])[CH:14]=2)[C:23]2[C:28](=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=2)[N:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Phosphorus tribromide (PBr3)(1.0 g) was added dropwise to a solution of ethyl 2-(2-hydroxyethyl)-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylate(1.7 g) in benzene (50 ml) at room temperature. The mixture was stirred at 80° C. for 1 hour, poured into ice-water, neutralized with an aqueous saturated sodium bicarbonate solution and extracted with chloroform. The chloroform layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform/ethyl acetate (1/1, v/v) gave ethyl 2-(2-bromoethyl)-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylate (0.49 g, 26%) which was then recrystallized from ethyl acetate-hexane. Colorless prisms. mp. 132°-133° C.

Workup

extractionextracted with chloroform
washThe chloroform layer was washed with water
dry with materialdried over magnesium sulfate
customthe solvent was evaporated
washThe fractions eluted with chloroform/ethyl acetate (1/1

Sources & evidence

ORD record: ord-262f2f5572b54e3398fd8d7c7f010c62
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05852039

Reaction notes

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