Pyridine → N-(5-chloropyridin-2-yl)-2-nitrobenzamide

HRID 644161

Reaction equation

HRID 644161 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.N1C=CC=CC=1.[N+:15]([C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21])([O-:17])=[O:16]>ClCCl>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:20](=[O:21])[C:19]2[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=2[N+:15]([O-:17])=[O:16])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 118752-Nitrobenzoyl chlorideHCID 661742-Amino-5-chloropyridine

Product 1

HCID 766647N-(5-chloropyridin-2-yl)-2-nitrobenzamideYield 79.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 2-amino-5-chloropyridine (3.7 g, 29 mmol) and pyridine (7.3 mL, 90 mmol) in dichloromethane (200 mL) was added 2-nitrobenzoyl chloride (5.7 g, 30 mmol). After stirring for 4 h, the solvents were removed in vacuo and the residue was partitioned between ethyl acetate and water. The layers were separated and the organic phase was washed again with water and once with brine, then dried with MgSO4, filtered and partially concentrated in vacuo. The precipitate was filtered, washed with diethyl ether and dried in vacuo to give 6.4 g (79%) of an off-white solid.

Workup

  1. customthe solvents were removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe layers were separated
  4. washthe organic phase was washed again with water and once with brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationpartially concentrated in vacuo
  8. filtrationThe precipitate was filtered
  9. washwashed with diethyl ether
  10. customdried in vacuo

Sources & evidence

ORD record
ord-651a8536c86b4bcdad9aab04bdc1ceaf
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Linked notes

Loading…