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

HRID 416640Notes

Reaction equation

HRID 416640 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 for 18 h. The dark mixture was then diluted with water (1500 mL) and sat. sodium bicarbonate solution was added until pH=8. The precipitate was collected by filtration, rinsed with water (30 mL×3) and dried in oven 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 pH=8
  2. filtrationThe precipitate was collected by filtration
  3. washrinsed with water (30 mL×3)
  4. customdried in oven

Sources & evidence

ORD record
ord-0c251b4166d5473da5eb085897e1560f
Source dataset
uspto-grants-2012_01
Patent number
US08088928B2

Reaction notes

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