Methanol → 2-Bromoquinoline-4-carboxylic acid

HRID 1823716Notes

Reaction equation

HRID 1823716 reaction equation
[Br:1][C:2]1(C(OC)=O)[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[OH-:16].[Na+].[CH3:18][OH:19]>O>[Br:1][C:2]1[CH:11]=[C:10]([C:18]([OH:19])=[O:16])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 22146649HCID 22146649, compound

Product 1

HCID 155506972-Bromoquinoline-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of methyl 2-bromoquinolinecarboxylate (7.2 g) and NaOH (1.1 g) in 15 mL of methanol and 15 mL of water is stirred at 50° C. until TLC indicates the disappearance of starting material. After cooling, the methanol is evaporated and the mixture is treated with 28 mL of 1N HCl, the solid is collected by filtration and dried to afford 6.1 g of 2-bromoquinoline-4-carboxylic acid.

Workup

  1. temperatureAfter cooling
  2. customthe methanol is evaporated
  3. additionthe mixture is treated with 28 mL of 1N HCl
  4. filtrationthe solid is collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-1fd621440982458da0050f773a99ffdd
Source dataset
uspto-grants-2006_05
Patent number
US07041664B2

Reaction notes

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