Sulfuric Acid → 2-(6-Chloro-5-methylpyridin-3-yl)acetic acid
Reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8]C#N)=[CH:4][C:3]=1[CH3:11].S(=O)(=O)(O)O.[C:17](=[O:20])([O-])[O-:18].[Na+].[Na+]>O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:17]([OH:18])=[O:20])=[CH:4][C:3]=1[CH3:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a flask containing 2-(6-chloro-5-methylpyridin-3-yl)acetonitrile 74-3 (1.12 g, 6.75 mmol) were added water (9.0 mL) and dropwise concentrated sulfuric acid (9.0 mL). The reaction mixture was stirred at 100° C. for 4 hours. After cooled down to room temperature, the reaction mixture was poured into water (100 mL). The resulting solution was neutralized with powder sodium carbonate to pH around 3, and extracted with ethyl acetate (50 mL×3). The combined organic layers were washed with brine, dried over Na2SO4 and then taken to dryness by rotary evaporation give 2-(6-Chloro-5-methylpyridin-3-yl)acetic acid 74-4 as pale yellow solid, which was used directly for next step. MS m/z 186.1 (M+1)
Workup
- temperatureAfter cooled down to room temperature
- extractionextracted with ethyl acetate (50 mL×3)
- washThe combined organic layers were washed with brine
- dry with materialdried over Na2SO4
- customtaken to dryness by rotary evaporation
Sources & evidence
- ORD record
- ord-73d8ae0d850a4e5485115fb532d60d12
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09238646B2
Reaction notes
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