4-Nitro-3-trifluoromethylphenol → 2-Amino-5-hydroxybenzotrifluoride

HRID 133739

Reaction equation

HRID 133739 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[C:11]([F:14])([F:13])[F:12])([O-])=O>C(O)(=O)C.[Zn]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[C:11]([F:12])([F:13])[F:14]

Participants

4

Reactant 1

HCID 69314-Nitro-3-trifluoromethylphenol

Product 1

HCID 146928342-Amino-5-hydroxybenzotrifluorideYield 59.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

4-Nitro-3-trifluoromethylphenol (0.414 g; 2.0 mmol) was dissolved in 25 ml of glacial acetic acid and zinc dust (2.62 g; 40 mmol) was added in small portions during 10 minutes allowing the temperature to rise up to +40° C. The mixture was stirred for ten minutes and filtered. The dust was washed with 3×10 ml of glacial acetic acid and filtrate was evaporated to dryness to give 0.212 g of 4-amino-3-trifluoromethylphenol. 1H NMR (400 MHz, DMSO-d6): 4.86 (2H, s), 6.72 (1H, d, J=8.7 Hz), 6.74 (1H, d, J=2.6 Hz), 6.78 (1H, dd, J=8.7 Hz, J=2.7 Hz), 8.91 (1H, s)

Workup

  1. customto rise up to +40° C
  2. filtrationfiltered
  3. washThe dust was washed with 3×10 ml of glacial acetic acid and filtrate
  4. customwas evaporated to dryness

Sources & evidence

ORD record
ord-916d2f6c3c90473e9bdfc9afb36a8971
Source dataset
uspto-grants-2008_06
Patent number
US07390923B2

Linked notes

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