Pyridine → N-(2-nitro-5-(pyrrolidin-1-yl)phenyl)benzamide

HRID 1888952Notes

Reaction equation

HRID 1888952 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][C:5]=1[NH2:15])([O-:3])=[O:2].N1C=CC=CC=1.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClCCl>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][C:5]=1[NH:15][C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 27602392-Nitro-5-(1-pyrrolidinyl)aniline

Product 1

HCID 68518954N-(2-nitro-5-(pyrrolidin-1-yl)phenyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-nitro-5-(pyrrolidin-1-yl)benzenamine (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 as eluent to afford N-(2-nitro-5-(pyrrolidin-1-yl)phenyl)benzamide as a solid.

Workup

  1. customThe solvent was evaporated in vacuum
  2. additiona mixture of hexanes and CH2Cl2 as eluent

Sources & evidence

ORD record
ord-0b713e48a7dd4a88859ea0258a33bdbd
Source dataset
uspto-grants-2013_08
Patent number
US08501957B2

Reaction notes

Loading…