Boron tribromide → HCID 86732831, compound

HRID 525967Notes

Reaction equation

HRID 525967 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([O:16]C)=[C:11]([O:14]C)[CH:12]=3)[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.B(Br)(Br)Br>ClCCl.CO>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([OH:16])=[C:11]([OH:14])[CH:12]=3)[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 82250420HCID 82250420, compound

Product 1

HCID 86732831HCID 86732831, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-cyclopropyl-6,7-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (10 g, 34.6 mmol) in Dichloromethane (DCM) (150 mL) was added BBr3 (16.34 mL, 173 mmol) at −78° C. The mixture was allowed to warm up to rt, and stirred at rt overnight. LCMS indicated completion of the reaction. The mixture was diluted with MeOH and concentrated. This procedure was repeated several times to afford 1-cyclopropyl-6,7-dihydroxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (8.2 g, 31.4 mmol, 91% yield) as yellow solid. The crude product was used in next step reaction without further purification.

Workup

  1. customcompletion of the reaction
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-c324aea33cf544bbb4ff2b569ef6f4d8
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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