Hydrogen Bromide → 6-Chloro-7-hydroxy-3,4-dihydrocarbostyril

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12]C)[NH:8][C:7](=[O:14])[CH2:6][CH2:5]2.Br>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[NH:8][C:7](=[O:14])[CH2:6][CH2:5]2

Participants

Reactant 2

HCID 260Hydrogen Bromide

HCID 128994196-Chloro-7-methoxy-3,4-dihydrocarbostyril

Product 1

HCID 128994206-Chloro-7-hydroxy-3,4-dihydrocarbostyrilYield 89.2%

Procedure

The thus obtained 30 g of 6-chloro-7-methoxy-3,4-dihydrocarbostyril are dispersed in 300 ml of 47%-hydrobromic acid aqueous solution and heated for 4 hours under refluxing condition. After cooling of the reaction mixture, the insoluble matter is separated by filtration, washed with water and dried. Recrystallization from methanol-chloroform obtains 25 g of 6-chloro-7-hydroxy-3,4-dihydrocarbostyril in the form of colorless needle-like crystals with a melting point of 264°-266° C.

Workup

temperatureheated for 4 hours
temperatureunder refluxing condition
temperatureAfter cooling of the reaction mixture
customthe insoluble matter is separated by filtration
washwashed with water
customdried
customRecrystallization from methanol-chloroform

Sources & evidence

ORD record: ord-251c2e40210443f89660a946d76ce883
Source dataset: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04734416

Reaction notes

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