Potassium Carbonate → Acetamide, N-(3-hydroxy-4-nitrophenyl)-

HRID 1773555Notes

Reaction equation

HRID 1773555 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([N+:15]([O-:17])=[O:16])=[C:9]([O:11]C(=O)C)[CH:10]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO>[OH:11][C:9]1[CH:10]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:6]=[CH:7][C:8]=1[N+:15]([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 127921275-Acetamido-2-nitrophenyl acetate

Product 1

HCID 10176525Acetamide, N-(3-hydroxy-4-nitrophenyl)-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of acetic acid 5-acetylamino-2-nitro-phenyl ester (20.5 g, 85.77 mmol) and potassium carbonate (26 g, 188.4 mmol) in methanol (200 mL) was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, water (250 mL) was added and the resulting mixture was acidified by addition of concentrated hydrochloric acid. The solid which crushed out was triturated, collected by filtration, washed with water and dried under vacuum to afford N-(3-hydroxy-4-nitro-phenyl)-acetamide.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, water (250 mL)
  2. additionwas added
  3. additionthe resulting mixture was acidified by addition of concentrated hydrochloric acid
  4. customThe solid which crushed out
  5. customwas triturated
  6. filtrationcollected by filtration
  7. washwashed with water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-d5291b0c53284b099630f211e21abe93
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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