Pyridine → N-Methyl-N-(4-nitrophenyl)acetamide

HRID 2263100Notes

Reaction equation

HRID 2263100 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.N1C=CC=CC=1.[C:18](Cl)(=[O:20])[CH3:19]>O1CCCC1>[CH3:1][N:2]([C:3]1[CH:4]=[CH:5][C:6]([N+:9]([O-:11])=[O:10])=[CH:7][CH:8]=1)[C:18](=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 7483N-Methyl-4-nitroaniline

Product 1

HCID 67143N-Methyl-N-(4-nitrophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-methyl-4-nitroaniline (5.00 g, 32.9 mmol) and pyridine (7.97 ml, 98.6 mmol) in tetrahydrofuran (100 ml) was added acetyl chloride (3.51 ml, 49.4 mmol) with ice-cooling, the mixture was stirred for 3 hours with ice-cooling, the reaction mixture was poured into ice-water and the desired product (2.60 g, 40.7%) as a solid was collected by filtration.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. filtrationthe desired product (2.60 g, 40.7%) as a solid was collected by filtration

Sources & evidence

ORD record
ord-9ac3b9cc9ce8487b953f9c7ee630e3b4
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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