Chlorosuccinimide → 5-Chloro-6-hydroxynicotinic acid
Reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[Cl:11]N1C(=O)CCC1=O>CC#N>[Cl:11][C:10]1[C:2](=[O:1])[NH:3][CH:4]=[C:5]([C:6]([OH:8])=[O:7])[CH:9]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 6-hydroxy nicotinic acid (0.500 g, 3.59 mmol, TCI) in MeCN (20 mL), was added N-chlorosuccinimide (0.436 mL, 5.39 mmol, Aldrich). The resulting mixture was then heated at 80° C. for 72 h. A white precipitate was present. The mixture was filtered and the white solid was washed with EtOAc (2×1 mL) and dried in vacuo to afford the title compound as a white solid. MS (ESI, positive ion) m/z: 174, 176 (M+H).
Workup
- filtrationThe mixture was filtered
- washthe white solid was washed with EtOAc (2×1 mL)
- customdried in vacuo
Sources & evidence
- ORD record
- ord-020be8896cb94c108095ec66a7d6f844
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08710043B2
Reaction notes
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