Acetic Acid → Acetamide, N-(2-methoxy-5-nitrophenyl)-

HRID 273936

Reaction equation

HRID 273936 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:11][CH3:12].[C:13](O)(=[O:15])[CH3:14].C(OC(=O)C)(=O)C>O>[C:13]([NH:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:11][CH3:12])(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 74472-Methoxy-5-nitroanilineHCID 7918Acetic Anhydride

Product 1

HCID 97239Acetamide, N-(2-methoxy-5-nitrophenyl)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

504 g (3 mol) of 2-amino-4-nitro-1-methoxybenzene are introduced into 860 ml of acetic acid and 600 ml of water (or the combined main filtrate and first wash filtrate of a previous batch) and the mixture is heated to 80° C. 358 g (3.2 mol) of acetic anhydride are added dropwise in the course of 10 minutes. The mixture is subsequently stirred at 80° C. for 4 hours, and then cooled to room temperature, while stirring, by removing the heating bath and finally to 15° C. The pale yellow needles which have precipitated are filtered off with suction, washed with 300 ml of 60% strength acetic acid and 1500 ml of water in several portions and dried.

Workup

  1. temperaturecooled to room temperature
  2. stirringwhile stirring
  3. customby removing the heating bath
  4. customfinally to 15° C
  5. customThe pale yellow needles which have precipitated
  6. filtrationare filtered off with suction
  7. washwashed with 300 ml of 60% strength acetic acid and 1500 ml of water in several portions
  8. customdried

Sources & evidence

ORD record
ord-81e010c1cada4efabc4550a7a913a1fe
Source dataset
uspto-grants-1995_02
Patent number
US05387716

Linked notes

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