2,3-Dimethyl-4-nitrophenol → 4-Hydroxyxylidine

HRID 1864665Notes

Reaction equation

HRID 1864665 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([N+:9]([O-])=O)[CH:5]=[CH:4][C:3]=1[OH:12]>CCO>[NH2:9][C:6]1[CH:5]=[CH:4][C:3]([OH:12])=[C:2]([CH3:1])[C:7]=1[CH3:8]

Participants

3

Reactant 1

HCID 133312452,3-Dimethyl-4-nitrophenol

Product 1

HCID 765424-HydroxyxylidineYield 972%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,3-dimethyl-4-nitrophenol (2 g, 1.2 mmol) and Pd(C) (10%) (1.83 g) in EtOH (80 mL) was stirred at room temperature under H2 atmosphere for 5 hours. The crude mixture was then filtered using celite and washed with DCM. After evaporating the solvent, the title compound (1.60 g, 97%) was obtained as a brown powder. 1H-NMR (6, ppm, DMSO-d6): 1.94 (s, 3H, HMe), 2.01 (s, 3H, HMe), 4.06 (s, 2H, NH2), 6.32 (d, 1H, Harom 6, J6-5=8.1 Hz), 6.40 (d, 1H, Harom 5, J6-5=8.1 Hz), 6.61 (s, 1H, Harom 2), 8.10 (broad s, 1H, OH).

Workup

  1. filtrationThe crude mixture was then filtered
  2. washwashed with DCM
  3. customAfter evaporating the solvent

Sources & evidence

ORD record
ord-4c501385014a41e3aeb28ddbc68ead4f
Source dataset
uspto-grants-2009_12
Patent number
US07625922B2

Reaction notes

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