Ethanol → 5-Bromo-3-methylpyridine-2-carboxylic acid
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4](C)[C:5](C#N)=[N:6][CH:7]=1.[OH-:11].[Na+].[CH2:13]([OH:15])[CH3:14]>O>[Br:1][C:2]1[CH:3]=[C:4]([CH3:5])[C:14]([C:13]([OH:11])=[O:15])=[N:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 5-bromo-3-methylpyridine-2-carbonitrile (3.9 g, 20 mmol) in ethanol (30 mL) was added 6.0 M sodium hydroxide in water (15 mL), and the reaction was stirred at 80° C. for 1.5 h. The reaction mixture was concentrated, diluted with water and partitioned in EtOAc. The aqueous phase was acidified to pH 2-3. The product then was extracted with EtOAc, washed with brine, dried over sodium sulfate, filtered and concentrated to give 4.2 g (98% yield) of the desired product as a yellow solid.
Workup
- concentrationThe reaction mixture was concentrated
- additiondiluted with water
- custompartitioned in EtOAc
- extractionThe product then was extracted with EtOAc
- washwashed with brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-42d5aabd18344f79b54970cdd1038d4b
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08895571B2
Reaction notes
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