Boron tribromide → 6-Hydroxyquinoline-3-carboxylic acid

HRID 340415Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([C:13]([OH:15])=[O:14])=[CH:6]2.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([C:13]([OH:15])=[O:14])=[CH:6]2

Participants

Conditions

Temperature: -78 °C

Procedure

6-Methoxyquinoline-3-carboxylic acid (2.5 g, 12.3 mmol) was suspended in anhydrous dichloromethane (20 mL) under nitrogen; the suspension was cooled to −78° C. A solution of BBr3 in dichloromethane (100 mL of 1M solution, 100 mmol) was added dropwise. The mixture was stirred for 30 min at −78° C., warmed slowly to RT, and allowed to stir at room temperature overnight. The reaction was quenched by dropwise addition of ice-water. The resulting solids were collected by filtration, and washed with water to yield 3.2 g (97%) of 6-hydroxyquinoline-3-carboxylic acid as an HBr salt. LCMS: >98%; MS: 190.27 (M+1, free base).

Workup

temperaturewarmed slowly to RT
stirringto stir at room temperature overnight
customThe reaction was quenched by dropwise addition of ice-water
filtrationThe resulting solids were collected by filtration
washwashed with water

Sources & evidence

ORD record: ord-f76360487f46472fa37281f53d42fbe3
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895578B2

Reaction notes

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