Methanol → 2-Bromoquinoline-4-carboxylic acid

HRID 2181607Notes

Reaction equation

HRID 2181607 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-b3a45560bfa14ac4b0d8b345f96c9eec
Source dataset
uspto-grants-2005_05
Patent number
US06894044B2

Reaction notes

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