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

HRID 403650Notes

Reaction equation

HRID 403650 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[OH:18].C(O)(=O)C>O>[OH:18][C:10]1[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=1[NH:8][C:5](=[O:7])[CH3:6]

Participants

5

Reactant 3

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

Product 1

HCID 3749260N-(2-Hydroxy-4-nitrophenyl)acetamideYield 92.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Acetic anhydride (79.6 g, 0.76 mol, 1.46 equiv) was added over 1.5 hours to the mixture of 2-amino-5-nitrophenol (80 g, 0.52 mol, 1.00 equiv) and acetic acid (320 ml, 5.2 mol, 10 equiv) at 60° C. After 1 hour, additional acetic anhydride was added (7.4 g, 0.071 mol, 0.137 equiv). After another 1 hour, the mixture was cooled and diluted with 200 ml of water. Solid was formed and collected by filtration and washed with water and heptane. The solid was dried in a vacuum oven to give the title compound 94 g. MS (ESI) m/z: 197 (M+1).

Workup

  1. waitAfter another 1 hour
  2. temperaturethe mixture was cooled
  3. customSolid was formed
  4. filtrationcollected by filtration
  5. washwashed with water and heptane
  6. customThe solid was dried in a vacuum oven

Sources & evidence

ORD record
ord-f24225a15a114a7ba5a11325f15c63ad
Source dataset
uspto-grants-2014_06
Patent number
US08748453B2

Reaction notes

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