m-Chloroperbenzoic acid → 3-Chloro-4-cyano-5-(3-methoxyphenyl)pyridine 1-oxide

HRID 81044Notes

Reaction equation

HRID 81044 reaction equation
[Cl:1][C:2]1[CH:9]=[N:8][CH:7]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=2)[C:3]=1[C:4]#[N:5].ClC1C=CC=C(C(OO)=[O:26])C=1>ClCCl>[Cl:1][C:2]1[CH:9]=[N+:8]([O-:26])[CH:7]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=2)[C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 669269143-Chloro-5-(3-methoxyphenyl)isonicotinonitrile

Product 1

HCID 669270323-Chloro-4-cyano-5-(3-methoxyphenyl)pyridine 1-oxideYield 93.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-chloro-5-(3-methoxyphenyl)isonicotinonitrile (1.60 g, 6.54 mmol) and 77% 3-chloroperbenzoic acid (5.86 g, 26.2 mmol) in dichloromethane (60 mL) was stirred at room temperature for 16 h. The mixture was diluted with dichloromethane (100 mL), washed with 1 M sodium sulfite (25 mL), 1 N NaOH (2×25 mL), brined (25 mL), dried (MgSO4) and concentrated to give crude 3-chloro-4-cyano-5-(3-methoxyphenyl)pyridine 1-oxide as white solid (1.60 g). The crude material was used in the next step without purification. MS (ES+) m/z: 261 (M+H); LC retention time: 2.933 min (analytical HPLC Method A).

Workup

  1. washwashed with 1 M sodium sulfite (25 mL), 1 N NaOH (2×25 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-01e9a98f37804b438be4de85d5e02223
Source dataset
uspto-grants-2014_09
Patent number
US08846673B2

Reaction notes

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