Methanol → Acetamide, N-(2-hydroxy-5-nitrophenyl)-

HRID 1106873Notes

Reaction equation

HRID 1106873 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].[C:12](OC(=O)C)(=[O:14])[CH3:13].CO>O1CCCC1>[C:12]([NH:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11])(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 36133892-Amino-4-Nitrophenol

Product 1

HCID 3292867Acetamide, N-(2-hydroxy-5-nitrophenyl)-Yield 95.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-Amino-4-nitrophenol (10 g, 0.065 mol) was dissolved in tetrahydrofuran (100 ml) and, after cooling to 0° C., acetic anhydride (12.24 ml, 0.130 mol) was added dropwise, followed by stirring at room temperature for 2 h. Thereafter, methanol (10 ml) was added to the reaction mixture, which was then stirred at room temperature for 30 min and, thereafter, the solvent was evaporated and the resulting residue was diluted with diethyl ether and filtered. The solvent was evaporated off the filtrate and the resulting solids were dried to yield the end compound 2-acetamido-4-nitrophenol (12.21 g) as a pale brown solid mass.

Workup

  1. stirringwas then stirred at room temperature for 30 min
  2. customthe solvent was evaporated
  3. additionthe resulting residue was diluted with diethyl ether
  4. filtrationfiltered
  5. customThe solvent was evaporated off the filtrate
  6. customthe resulting solids were dried

Sources & evidence

ORD record
ord-5703df76c6e44a5f88697dcf2a49ac0f
Source dataset
uspto-grants-2000_05
Patent number
US06057358

Reaction notes

Loading…