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

HRID 862632Notes

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-4933e5c2fb9a4ae69ab079eaf8956ae7
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05719157

Reaction notes

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