2-Nitrobenzoyl chloride → N-(2-chloro-5-methylpyridin-3-yl)-2-nitrobenzamide

HRID 2387399Notes

Reaction equation

HRID 2387399 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[N:6][C:7]=1[Cl:8].[N+:10]([C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15](Cl)=[O:16])([O-:12])=[O:11]>N1C=CC=CC=1.O.C(=O)(O)[O-].[Na+]>[Cl:8][C:7]1[C:2]([NH:1][C:15](=[O:16])[C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=2[N+:10]([O-:12])=[O:11])=[CH:3][C:4]([CH3:9])=[CH:5][N:6]=1

Participants

6

Reactant 2

HCID 118752-Nitrobenzoyl chlorideHCID 27344222-Chloro-5-methylpyridin-3-amine

Product 1

HCID 15654865N-(2-chloro-5-methylpyridin-3-yl)-2-nitrobenzamideYield 91%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 5-amino-6-chloro-3-picoline (9.54 g, 66.9 mmol) in pyridine (200 mL) was added 2-nitrobenzoyl chloride (13.65 g, 73.6 mmol) dropwise at 0° C. The resulting mixture was stirred at room temperature (18 h). The dark mixture was then diluted with water (1500 mL) and sat. sodium bicarbonate solution was added until the pH reached 8. The precipitate was collected by filtration, rinsed with water (30 mL×3) and dried to afford N-(2-chloro-5-methylpyridin-3-yl)-2-nitrobenzamide as a pale solid (17.70 g, yield: 91%).

Workup

  1. additionwas added until the pH
  2. filtrationThe precipitate was collected by filtration
  3. washrinsed with water (30 mL×3)
  4. customdried

Sources & evidence

ORD record
ord-4502e27c35b247bd9cfdb0ab29df0100
Source dataset
uspto-grants-2012_09
Patent number
US08268862B2

Reaction notes

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