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

HRID 1883037Notes

Reaction equation

HRID 1883037 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 was added 2-nitrobenzoyl chloride (5.7 g, 30 mmol). After stirring for 4 h, the solvents were removed in vacuo and the residue partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. After standing at room temperature overnight, the mixture was filtered to give 6.4 g (79%) of a white solid.

Workup

  1. customthe solvents were removed in vacuo
  2. customthe residue partitioned between ethyl acetate and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. waitAfter standing at room temperature overnight
  8. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-ab5abf13573e47d98d10ac43babf9570
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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