Chlorosuccinimide → 5-Chloro-6-hydroxynicotinic acid

HRID 509386Notes

Reaction equation

HRID 509386 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]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 178418479HCID 178418479, compound

Product 1

HCID 5995415-Chloro-6-hydroxynicotinic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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

  1. filtrationThe mixture was filtered
  2. washthe white solid was washed with EtOAc (2×1 mL)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-ca1438b71a324847a8d9190f6b051e68
Source dataset
uspto-grants-2015_08
Patent number
US09096527B2

Reaction notes

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