Acetic Anhydride → Acetamide, N-(2-methyl-3-nitrophenyl)-

HRID 394574Notes

Reaction equation

HRID 394574 reaction equation
[CH3:1][C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:12](OC(=O)C)(=[O:14])[CH3:13]>C1COCC1>[C:12]([NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[C:8]([N+:9]([O-:11])=[O:10])[C:2]=1[CH3:1])(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 117832-Methyl-3-nitroaniline

Product 1

HCID 151316Acetamide, N-(2-methyl-3-nitrophenyl)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

84 g of 2-methyl-3-nitroaniline is dissolved in 550 ml of THF. 53 ml of acetic anhydride is slowly added dropwise and the mixture is then stirred at 70° C. After about 1 hour, THF is distilled off and the residue is combined with 250 ml of petroleum ether. The solid precipitate is filtered off and dried at 50° C. 106 g of N-acetyl-2-methyl-3-nitroaniline is obtained as a light brown powder.

Workup

  1. distillationTHF is distilled off
  2. filtrationThe solid precipitate is filtered off
  3. customdried at 50° C

Sources & evidence

ORD record
ord-b71a23e3b2154d39afd5ef12af7675d8
Source dataset
uspto-grants-2003_08
Patent number
US06602897B2

Reaction notes

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