Sodium Dithionite → 2-Amino-6-isopropylphenol

HRID 897946Notes

Reaction equation

HRID 897946 reaction equation
[CH:1]([C:4]1[C:9]([OH:10])=[C:8]([N+:11]([O-])=O)[CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(O)C.O>[NH2:11][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:1]([CH3:2])[CH3:3])[C:9]=1[OH:10]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 5289552-Isopropyl-6-nitrophenol

Product 1

HCID 146849822-Amino-6-isopropylphenolYield 72%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 6-isopropyl-2-nitrophenol (3.000 g, 16.56 mmol) and sodium hydrosulfite (11.53 g, 66.23 mmol) in ethanol (180 mL) and water (90 mL) was stirred at 80° C. for 20 h and then cooled to room temperature. The resulting orange solution was concentrated and then partitioned between dichloromethane (50 mL) and water (50 mL). The organic phase was separated and washed with brine (25 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated to afford 2-amino-6-isopropylphenol as an orange solid (1.792 g, 72%). RP-HPLC Rt 8.171 min, 92% purity (5% to 85% acetonitrile/0.1M aqueous ammonium acetate, buffered to pH 4.5, over 20 min at 1 mL/min; λ=254 nm; Deltapak C18, 300 A, 5 μm, 150×3.9 mm column); m/z 150 (M−H)−.

Workup

  1. concentrationThe resulting orange solution was concentrated
  2. custompartitioned between dichloromethane (50 mL) and water (50 mL)
  3. customThe organic phase was separated
  4. washwashed with brine (25 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-34bb8e4c4ac3437c8bd6a7731d701e03
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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