1-(4-Methyl-3-nitrophenyl)ethan-1-ol → 1-(3-Amino-4-methylphenyl)ethan-1-ol

HRID 2410001Notes

Reaction equation

HRID 2410001 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:11][C:3]1[CH:4]=[C:5]([CH:8]([OH:10])[CH3:9])[CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

4

Reactant 1

HCID 434983221-(4-Methyl-3-nitrophenyl)ethan-1-ol

Product 1

HCID 120512021-(3-Amino-4-methylphenyl)ethan-1-olYield 97.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(4-methyl-3-nitrophenyl)ethan-1-ol (1.96 g) in ethyl acetate (55 mL) was added 10% palladium on carbon (56.5% water included, 901 mg), and the mixture was stirred at room temperature for 7 hours under a hydrogen atmosphere. The reaction mixture was filtered through celite (registered trademark) pad. The filtrate was concentrated under reduced pressure to obtain the title compound (1.60 g). 1H-NMR (CDCl3) δ ppm: 1.47 (3H, d, J=6.4 Hz), 1.73 (1H, br s), 2.16 (3H, s), 3.63 (2H, br s), 4.80 (1H, q, J=6.4 Hz), 6.66-6.75 (2H, m), 7.02 (1H, d, J=7.3 Hz).

Workup

  1. filtrationThe reaction mixture was filtered through celite (registered trademark) pad
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6d67097930aa4b68bcec4c3dbc387f9d
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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