Hydrazine hydrate (1:1) → 1-(4-Aminophenyl)-2,2,2-trifluoroethan-1-ol

HRID 2235133Notes

Reaction equation

HRID 2235133 reaction equation
[F:1][C:2]([F:15])([F:14])[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][CH:6]=1)[OH:4].O.NN>C(O)C.O1CCCC1.[Pd]>[NH2:11][C:8]1[CH:9]=[CH:10][C:5]([CH:3]([OH:4])[C:2]([F:1])([F:14])[F:15])=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 115286532,2,2-trifluoro-1-(4-nitrophenyl)ethanol

Product 1

HCID 126403421-(4-Aminophenyl)-2,2,2-trifluoroethan-1-ol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,2,2-trifluoro-1-(4-nitro-phenyl)-ethanol (2.0 g, 9 mmol) in ethanol (100 ml) and tetrahydrofuran (37 ml) was treated under argon with Pd/C (250 mg) and hydrazine hydrate (80% in water, 6.15 ml, 127 mmol, 14 equiv.) The mixture was stirred at room temperature for 30 min, then the black solid was filtered and the solvent evaporated. 1-(4-Amino-phenyl)-2,2,2-trifluoro-ethanol was obtained as a light yellow deliquescent solid, 1.8 g (100%). δH (300 MHz; CDCl3) 7.24 (2H, d), 6.67 (2H, d), 4.87 (1H, m), 3.72 (2H, bs), 3.32 (1H, bs).

Workup

  1. filtrationthe black solid was filtered
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-bff65628a9d8444ebe90af8018870829
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

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