Acetic Acid → N-(2-Hydroxy-4-nitrophenyl)acetamide

HRID 748622Notes

Reaction equation

HRID 748622 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].[C:12](O)(=[O:14])[CH3:13].C(OC(=O)C)(=O)C>O>[C:12]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11])(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic Anhydride2×HCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 3749260N-(2-Hydroxy-4-nitrophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 400 g of 2-amino-5-nitrophenol in a 5-L multi-necked flask equipped with a mechanical stirrer, reflux condenser, nitrogen inlet, 500-mL addition funnel, heating mantle, and a thermocouple attached to a temperature controller was added 1.6 L of acetic acid. The mixture was stirred at 60° C. as 398 g of acetic anhydride was added over 1.5 hours. After 1 hour, another 37 g of acetic anhydride was added. After another 1 hour, the mixture was cooled and diluted with 2 L of water. Solid was collected by filtration and washed with water and heptane. The solid was dried in a vacuum oven to give 509 g of the title compound.

Workup

  1. temperaturereflux
  2. additioncondenser, nitrogen inlet, 500-mL addition funnel
  3. temperatureheating mantle
  4. additionwas added over 1.5 hours
  5. waitAfter another 1 hour
  6. temperaturethe mixture was cooled
  7. filtrationSolid was collected by filtration
  8. washwashed with water and heptane
  9. customThe solid was dried in a vacuum oven

Sources & evidence

ORD record
ord-be7b0a8c400f4e5b82f5db69f6489fef
Source dataset
uspto-grants-2008_07
Patent number
US07399865B2

Reaction notes

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