Toluene → Acetamide, N-(2-hydroxy-5-nitrophenyl)-

HRID 2398760Notes

Reaction equation

HRID 2398760 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].C1(C)C=CC=CC=1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>C(O)(=O)C>[C:19]([NH:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 1140TolueneHCID 7918Acetic AnhydrideHCID 36133892-Amino-4-Nitrophenol

Product 1

HCID 3292867Acetamide, N-(2-hydroxy-5-nitrophenyl)-

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 10 g. (0.065 mol) of 2-amino-4-nitrophenol, 125 ml. of dry toluene and 25 ml. of glacial acetic acid is heated to affect solution. Acetic anhydride (7.57 g., 0.074 mol) is added dropwise over a period of twenty minutes and the resulting mixture is heated at about 80° C. for two hours. The reaction mixture is filtered and the solid is washed with toluene, then recrystallized from methanol to give 2-acetamido-4-nitrophenol, m.p. 283°-284° C.

Workup

  1. additionA mixture of 10 g
  2. filtrationThe reaction mixture is filtered
  3. washthe solid is washed with toluene
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-a166097cefd742119faa5bf69fbff06c
Source dataset
uspto-grants-1977_05
Patent number
US04025642

Reaction notes

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