Stannous Chloride → 2-Amino-6-(trifluoromethyl)phenol

HRID 650104Notes

Reaction equation

HRID 650104 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-])=O)[C:4]=1[OH:12].[Sn](Cl)Cl.C([O-])(O)=O.[Na+]>C(O)C>[F:1][C:2]([F:13])([F:14])[C:3]1[C:4]([OH:12])=[C:5]([CH:6]=[CH:7][CH:8]=1)[NH2:9]

Participants

5

Reactant 3

HCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 9018342-Nitro-6-(trifluoromethyl)phenol

Product 1

HCID 222727462-Amino-6-(trifluoromethyl)phenolYield 94.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the solution of 2-trifluoromethyl-6-nitrophenol (4.2 g, 20.3 mmol) in ethanol (20 ml, Tin (II) chloride (22.9 g, 101 mmol) was added. The reaction mixture was stirred at reflux for about 4 hours, tThen it was cooled to room temperature. The NaHCO3 (aq) was added until pH=7 was obtained and then the mixture was extracted with ethyl acetate (3×). The combined organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to give desired product (3.4 g, 94%). EI-MS m/z 178 (M+).

Workup

  1. temperatureat reflux for about 4 hours
  2. customwas obtained
  3. extractionthe mixture was extracted with ethyl acetate (3×)
  4. dry with materialThe combined organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d40dba022b53468bae684538432a761a
Source dataset
uspto-grants-2001_08
Patent number
US06271261B1

Reaction notes

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