Water → 6-Bromo-5-methylpyridine-2-carboxylic acid

HRID 927432Notes

Reaction equation

HRID 927432 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]#N)[CH:5]=[CH:4][C:3]=1[CH3:10].[OH-:11].[Na+].[OH2:13]>>[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:13])=[O:11])[CH:5]=[CH:4][C:3]=1[CH3:10]

Participants

4

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 219283226-Bromo-5-methylpyridine-2-carbonitrile

Product 1

HCID 717210026-Bromo-5-methylpyridine-2-carboxylic acidYield 63.8%

Conditions

Temperature
120 °C

Procedure

6-Bromo-5-methyl-pyridine-2-carbonitrile (1.0 g, 5.0 mmol) was added to a solution of sodium hydroxide (0.3 g, 7 mmol) in water (20 mL), the mixture was stirred at 120° C. overnight. Subsequently, the mixture was adjusted to pH=3 and extracted with ethyl acetate (2×15 mL). The organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated to give the product (0.7 g, 63.8%); MS (EI): m/e 216.0 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate (2×15 mL)
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-60082d51c75e4805827223e39e718796
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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