Acetyl chloride → 4-Nitroacetanilide

HRID 2280339Notes

Reaction equation

HRID 2280339 reaction equation
[C:1](Cl)([CH3:3])=[O:2].[N+:5]([C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)([O-:7])=[O:6]>C(Cl)Cl.N1C=CC=CC=1>[N+:5]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:1](=[O:2])[CH3:3])=[CH:10][CH:9]=1)([O-:7])=[O:6]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 74754-Nitroaniline

Product 1

HCID 76914-NitroacetanilideYield 97%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of Pyridine (3 mL) and AcCl (1.017 g, 13.043) in DCM (15 mL) was added the solution of 4-nitrobenzenamine (1.5 g, 10.870 mmol) in pyridine (3 mL) at 0° C. The mixture was stirred at room temperature for 1 h. The volatiles were removed under reduced pressure and the residue was washed with water (10 mL×3), dried under reduced pressure to afford N-(4-nitrophenyl)acetamide as yellow powder (1.9 g, yield: 97%).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. washthe residue was washed with water (10 mL×3)
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-b3d8216bcee741f3857e622592c1720b
Source dataset
uspto-grants-2015_09
Patent number
US09138427B2

Reaction notes

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