Water → N-(3-amino-4-methylphenyl)acetamide

HRID 1454286Notes

Reaction equation

HRID 1454286 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([CH3:18])=[C:9]([NH:11]C(=O)C(F)(F)F)[CH:10]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].O>CO>[NH2:11][C:9]1[CH:10]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:6]=[CH:7][C:8]=1[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 22393509N-(5-Acetylamino-2-methyl-phenyl)-2,2,2-trifluoro-acetamide

Product 1

HCID 22865N-(3-amino-4-methylphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(5-Acetylamino-2-methyl-phenyl)-2,2,2-trifluoro-acetamide (2.93 g, 11.24 mmol) was taken up in methanol (50 mL) and sodium carbonate (5.96 g, 56.20 mmol) was added. The reaction was stirred at room temp for 12 h. The reaction mixture was into water and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent removed under reduced pressure. The product was utilized without further purification. Yield 1.60 g. 1H NMR (CDCl3, 300 MHz): 82.16 (s, 3H). 2.31 (s, 3H), 7.18 (d, J=9 Hz, 1H), 7.32 (d, J=9 Hz, 1H), 7.64 (s, 1H).

Workup

  1. extractionthe aqueous layer was extracted three times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe solution was filtered
  5. customthe solvent removed under reduced pressure
  6. customThe product was utilized without further purification

Sources & evidence

ORD record
ord-c46f64f536d4423c8b29edd8c9eb1c02
Source dataset
uspto-grants-2009_01
Patent number
US07479495B2

Reaction notes

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