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

HRID 902445Notes

Reaction equation

HRID 902445 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 AnhydrideHCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 3749260N-(2-Hydroxy-4-nitrophenyl)acetamideYield 95.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
62.5 °C

Procedure

Acetic anhydride (398 g, 3.90 mol) was added to a stirred suspension of 2-amino-5-nitro-phenol (400 g, 2.60 mol) and acetic acid (1.60 L) at 62.5° C. The reaction mixture was stirred at 62.5° C. for 1 hour, and then cooled to room temperature. Water (2.00 L) was added over 20 minutes to the stirred reaction mixture. After stirring for 1 hour, the solid was collected by vacuum filtration and washed with water and heptane. Drying the product in vacuo at 60° C. yielded 486.7 g (96%, 99.5% by HPLC) of N-(2-hydroxy-4-nitro-phenyl)-acetamide. 1H NMR (DMSO-d6) δ (ppm) 2.18 (s, 3H), 7.70 (m, 2H), 8.30 (d, 1H), 9.45 (s, 1H), 11.00 (s, 1H).

Workup

  1. temperaturecooled to room temperature
  2. stirringAfter stirring for 1 hour
  3. filtrationthe solid was collected by vacuum filtration
  4. washwashed with water and heptane
  5. customDrying the product in vacuo at 60° C.

Sources & evidence

ORD record
ord-00ba2504103841a884e0cd6a6ceac140
Source dataset
uspto-grants-2008_04
Patent number
US07365203B2

Reaction notes

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