Water → N-(4-methoxyphenyl)-4-nitrobenzamide

HRID 1197865Notes

Reaction equation

HRID 1197865 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[N+:10]([C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1)([O-:12])=[O:11].O>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:17](=[O:18])[C:16]2[CH:15]=[CH:14][C:13]([N+:10]([O-:12])=[O:11])=[CH:21][CH:20]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7732P-AnisidineHCID 85024-Nitrobenzoyl chloride

Product 1

HCID 532159N-(4-methoxyphenyl)-4-nitrobenzamideYield 73.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

12.3 g of p-anisidine were added in small fractions to a suspension of 18.6 g of 4-nitrobenzoic acid chloride in 100 ml of pyridine and the mixture was heated for 2 hours at reflux. After returning to ambient temperature, the solution was poured into 500 ml of iced water and the precipitate formed was separated and washed with water, then dried under reduced pressure at 80° C. to obtain 20 g of N-(4-methoxyphenyl)-4-nitrobenzamide melting at 200° C.

Workup

  1. temperaturethe mixture was heated for 2 hours
  2. temperatureat reflux
  3. customAfter returning to ambient temperature
  4. customthe precipitate formed
  5. customwas separated
  6. washwashed with water
  7. customdried under reduced pressure at 80° C.

Sources & evidence

ORD record
ord-e2ae17e3f0a84d0298ab4ea40feda79d
Source dataset
uspto-grants-1994_01
Patent number
US05278180

Reaction notes

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