Boron tribromide → HCID 86732837, compound

HRID 525972Notes

Reaction equation

HRID 525972 reaction equation
[Cl:1][C:2]1[C:11]([OH:12])=[C:10]([O:13]C)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1.B(Br)(Br)Br>ClCCl.CO>[Cl:1][C:2]1[C:11]([OH:12])=[C:10]([OH:13])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:16][CH2:17]1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 86732836HCID 86732836, compound

Product 1

HCID 86732837HCID 86732837, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-chloro-1-cyclopropyl-6-hydroxy-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (8.5 g, 27.4 mmol) in Dichloromethane (DCM) (100 mL) was added BBr3 (6.49 mL, 68.6 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 to dryness. This procedure was repeated several times to afford 5-chloro-1-cyclopropyl-6,7-dihydroxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (7.8 g, 26.4 mmol, 96% yield) as yellow solid. LCMS: [M+H]+: 296.1.

Workup

  1. customcompletion of the reaction
  2. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-3b81fe0e348346cb821f8376b7a8b697
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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