Sodium Dithionite → 2-{[2-Amino-6-(trifluoromethyl)phenyl]amino}ethanol

HRID 1991200Notes

Reaction equation

HRID 1991200 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[C:5]=1[NH:14][CH2:15][CH2:16][OH:17])([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>CO.O>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:12])([F:13])[F:11])[C:5]=1[NH:14][CH2:15][CH2:16][OH:17]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 113571292-([2-Nitro-6-(trifluoromethyl)phenyl]amino}ethanol

Product 1

HCID 111953562-{[2-Amino-6-(trifluoromethyl)phenyl]amino}ethanolYield 89.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 2-{[2-nitro-6-(trifluoromethyl)phenyl]amino}ethanol (0.72 g, 2.88 mmol) in methanol (30 mL) a suspension of 85% sodium hydrosulfite (2.0 g, 9.8 mmol) in water (6 mL) was added. Additional water (4 mL) was added, and the mixture was heated at 60° C. for 15 min. The reaction mixture was cooled and concentrated in vacuo. The residue was extracted with ethyl acetate, and the organic phase was dried over magnesium sulfate. The solvent was removed in vacuo affording 0.57 g of 2-{[2-amino-6-(trifluoromethyl)phenyl]amino}ethanol: MS (ES) m/z 219 [M−H].

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated in vacuo
  4. extractionThe residue was extracted with ethyl acetate
  5. dry with materialthe organic phase was dried over magnesium sulfate
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-cea36f64a7de4acea5ec0ce77d5b489a
Source dataset
uspto-grants-2010_01
Patent number
US07645784B2

Reaction notes

Loading…