2-Nitro-4-(trifluoromethyl)phenol → 2-Amino-4-(trifluoromethyl)phenol

HRID 323111

Reaction equation

HRID 323111 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[C:5]([N+:10]([O-])=O)[CH:4]=1.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C>[NH2:10][C:5]1[CH:4]=[C:3]([C:2]([F:1])([F:13])[F:14])[CH:8]=[CH:7][C:6]=1[OH:9]

Participants

5

Reactant 3

HCID 98162-Nitro-4-(trifluoromethyl)phenolHCID 14798Sodium HydroxideHCID 24479Stannous Chloride

Product 1

HCID 1202462-Amino-4-(trifluoromethyl)phenolYield 83.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-trifluoromethyl-2-nitrophenol(1.0 g, 4.8 mmol) and tin (II) chloride (5.4 g, 24.2 mmol) in ethanol(150 mL) was heated at 80° C. under argon. After 2 hours, the starting material had disappeared and the solution was allowed to cool down and then poured into ice. The pH was made slightly basic (pH7-8), by addition of solid NaOH, before being extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4% MeOH/CH2Cl2) gave the desired product(708 mg, 83%). 1H NMR (CD3OD): d 6.87 (s, 1H), 6.80 (d, 1H), 6.69 (d, 1H).

Workup

  1. temperatureto cool down
  2. additionpoured into ice
  3. extractionbefore being extracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-69ca5bf0c43b45a5badc27606023348a
Source dataset
uspto-grants-2001_04
Patent number
US06211373B1

Linked notes

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