Pyridine → N-(4-Nitrophenyl)propionamide

HRID 2263235Notes

Reaction equation

HRID 2263235 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[N+:6]([C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)([O-:8])=[O:7].N1C=CC=CC=1>O1CCCC1>[N+:6]([C:9]1[CH:15]=[CH:14][C:12]([NH:13][C:1](=[O:4])[CH2:2][CH3:3])=[CH:11][CH:10]=1)([O-:8])=[O:7]

Participants

5

Reactant 3

HCID 1049PyridineHCID 74754-NitroanilineHCID 62324Propionyl chloride

Product 1

HCID 3627923N-(4-Nitrophenyl)propionamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Propionyl chloride (25.0 g, 270 mmol) was added dropwise to a solution of 4-nitroaniline (24.9 g, 180 mmol) and pyridine (43.7 ml, 540 mmol) in tetrahydrofuran (500 ml) under ice-cooling, the mixture was stirred under ice-cooling for 2 hour, and the solvent was distilled off under reduced pressure. The residue was poured into ice-water, and 33.5 g (95.7%) of the desired product was collected by filtration as a solid.

Workup

  1. temperaturecooling
  2. temperaturecooling for 2 hour
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionThe residue was poured into ice-water, and 33.5 g (95.7%) of the desired product
  5. filtrationwas collected by filtration as a solid

Sources & evidence

ORD record
ord-d968f1657c52418193dec281dcc64e76
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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