Water → 2-(2-Chloropyridin-3-yl)acetic acid
Reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][C:9]#N)=[CH:6][CH:5]=[CH:4][N:3]=1.S(=O)(=O)(O)[OH:12].[OH2:16]>>[Cl:1][C:2]1[C:7]([CH2:8][C:9]([OH:12])=[O:16])=[CH:6][CH:5]=[CH:4][N:3]=1Participants
4
Conditions
- Temperature
- 90 °C
Procedure
To a solution of the compound (11.7 g) obtained in step 3 in water (66 mL) was added concentrated sulfuric acid (55.6 mL) at 0° C., and the mixture was stirred at 90° C. for 4 hr. The reaction mixture was poured into ice-cold water, and the precipitate was filtered off. The filtrate was extracted three times with ethyl acetate. The organic layer was washed with brine, and concentrated to give (2-chloropyridin-3-yl)acetic acid (10.5 g, 80%) as a white powder.
Workup
- additionThe reaction mixture was poured into ice-cold water
- filtrationthe precipitate was filtered off
- extractionThe filtrate was extracted three times with ethyl acetate
- washThe organic layer was washed with brine
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-fd94997d6c22400aa17ee5542bdfc425
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08158617B2
Reaction notes
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