2-Nitro-6-phenylaminocarbonylphenol → 3-Amino-2-hydroxy-N-phenylbenzamide

HRID 1419418Notes

Reaction equation

HRID 1419418 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:11])[C:5]=1[OH:19])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([NH:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:11])[C:5]=1[OH:19]

Participants

4

Reactant 1

HCID 185513542-Nitro-6-phenylaminocarbonylphenol

Product 1

HCID 211848133-Amino-2-hydroxy-N-phenylbenzamideYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-nitro-6-phenylaminocarbonylphenol (1 g, 4.0 mmol) in methanol(250 mL) was added 10% Pd/C (100 mg). The mixture was flushed with argon, then hydrogen was bubbled through the solution for 10 min. and a hydrogen atmosphere was maintained at balloon pressure overnight. The mixture was filtered through celite and the celite was washed with methanol. The solvent was evaporated and chromatography of the resulting solid on silica gel (5% MeOH/CH2Cl2) gave the desired product(800 mg, 91%). 1H NMR (CD3OD): δ 7.73-7.57 (m, 2H), 7.43-7.27 (m, 3H), 7.25-7.10 (m, 1H), 6.94 (t, 1H), 6.74 (t, 1H).

Workup

  1. customThe mixture was flushed with argon
  2. customhydrogen was bubbled through the solution for 10 min.
  3. temperaturea hydrogen atmosphere was maintained at balloon pressure overnight
  4. filtrationThe mixture was filtered through celite
  5. washthe celite was washed with methanol
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-a47dfb88a5ac4d439bb01f2e2a33bc75
Source dataset
uspto-grants-1999_03
Patent number
US05886044

Reaction notes

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