m-Chloroperbenzoic acid → 3-Pyridinecarboxylic acid, 6-chloro-, 1-oxide

HRID 2245535Notes

Reaction equation

HRID 2245535 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][N:14]=1>C(Cl)(Cl)Cl>[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][N+:14]=1[O-:9]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 792226-Chloronicotinic acid

Product 1

HCID 114579603-Pyridinecarboxylic acid, 6-chloro-, 1-oxideYield 93%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
45 °C

Procedure

m-Chloroperbenzoic acid (7.46 g, 26.0 mmol) was added to a suspension of 6-chloronicotinic acid (3.14 g, 20.0 mmol) in chloroform (30 mL) at room temperature. The mixture was stirred for 24 h at 45° C. followed by cooling to 0° C. The resulting white precipitate was filtered off, washed with chloroform (10 mL), and air-dried to give 3.22 g, (93% yield) of the title compound: 1H NMR (DMSO-d6, 400 MHz) δ 8.72 (s, 1H), 7.97 (d, J=8.0 Hz, 1H), 7.78 (d, J=8.0 Hz, 1H); MS (EI) m/z 174 and 176 (M++1).

Workup

  1. temperatureby cooling to 0° C
  2. filtrationThe resulting white precipitate was filtered off
  3. washwashed with chloroform (10 mL)
  4. customair-dried

Sources & evidence

ORD record
ord-12570f8ded7b40b699cc6121f67daf9c
Source dataset
uspto-grants-2010_03
Patent number
US07683067B2

Reaction notes

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