Benzoyl chloride, 3-nitro- → 3-Nitro-N-(3-pyridinylmethyl)benzamide

HRID 1900018Notes

Reaction equation

HRID 1900018 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7](Cl)=[O:8])([O-:3])=[O:2].C(=O)(O)[O-].[Na+].[NH2:18][CH2:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1>C(OCC)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([NH:18][CH2:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)=[O:8])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8495Benzoyl chloride, 3-nitro-HCID 310183-PyridinemethanamineHCID 516892Sodium Bicarbonate

Product 1

HCID 7434213-Nitro-N-(3-pyridinylmethyl)benzamideYield 46%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred two-phase solution of 3-nitrobenzoyl chloride (9.3 g) in a mixture of diethyl ether (50 ml) and saturated sodium bicarbonate solution (50 ml) was added 3-aminomethylpyridine (5.4 g) in an ice-cooled bath. The mixture was stirred vigorously at ambient temperature for 30 minutes. The reaction mixture was filtered, and the resulting solid was washed with water. The solid was further solidified with diisopropyl alcohol-water to afford 3-nitro-N-(3-pyridylmethyl)benzamide (5.91 g) as a pale yellow amorphous solid.

Workup

  1. temperaturecooled bath
  2. filtrationThe reaction mixture was filtered
  3. washthe resulting solid was washed with water

Sources & evidence

ORD record
ord-f1f5bdaec2b5413a8bb1e72e0fb59576
Source dataset
uspto-grants-1996_11
Patent number
US05574042

Reaction notes

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