Pyridine → N-(5-methyl-2-nitrophenyl)benzamide

HRID 1888947Notes

Reaction equation

HRID 1888947 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].N1C=CC=CC=1.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>ClCCl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH:7][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:8]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 113566-Nitro-m-toluidine

Product 1

HCID 68517695N-(5-methyl-2-nitrophenyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-methyl-2-nitroaniline (4 mmol) and pyridine (8 mmol) in dry dichloromethane (15 mL) was added dropwise benzoyl chloride (8 mmol). The reaction mixture was stirred at room temperature for 8 h. The solvent was evaporated in vacuum, and the residue was subjected to flash chromatography on silica gel using a mixture of hexanes and CH2Cl2 (7:3) as eluent to afford N-(5-methyl-2-nitrophenyl)benzamide as a solid.

Workup

  1. customThe solvent was evaporated in vacuum
  2. additiona mixture of hexanes and CH2Cl2 (7:3) as eluent

Sources & evidence

ORD record
ord-8990f231fc2b4c9fa2f6729f34457a67
Source dataset
uspto-grants-2013_08
Patent number
US08501957B2

Reaction notes

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