2-(3-Isopropyl-4-hydroxy-phenoxy)-3-methyl-5-nitrobenzonitrile → 5-Amino-2-(3-isopropyl-4-hydroxy-phenoxy)-3-methyl-benzonitrile

HRID 636716Notes

Reaction equation

HRID 636716 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[OH:23])[O:7][C:8]1[C:15]([CH3:16])=[CH:14][C:13]([N+:17]([O-])=O)=[CH:12][C:9]=1[C:10]#[N:11])([CH3:3])[CH3:2]>C(O)C>[NH2:17][C:13]1[CH:14]=[C:15]([CH3:16])[C:8]([O:7][C:6]2[CH:20]=[CH:21][C:22]([OH:23])=[C:4]([CH:1]([CH3:2])[CH3:3])[CH:5]=2)=[C:9]([CH:12]=1)[C:10]#[N:11]

Participants

3

Reactant 1

HCID 155236452-(3-Isopropyl-4-hydroxy-phenoxy)-3-methyl-5-nitrobenzonitrile

Product 1

HCID 155236465-Amino-2-(3-isopropyl-4-hydroxy-phenoxy)-3-methyl-benzonitrileYield 77.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(3-isopropyl-4-hydroxy-phenoxy)-3-methyl-5-nitrobenzonitrile (215 mg) and stannous chloride (776 mg) in ethanol (5 mL) was refluxed for 2 h, cooled, quenched with saturated aqueous sodium bicarbonate and concentrated in vacuo. The residue was extracted with ethyl acetate, the organics washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was flash chromatographed (40% ethyl acetate/hexanes) to afford 5-amino-2-(3-isopropyl-4-hydroxy-phenoxy)-3-methyl-benzonitrile as a colorless foam (150 mg).

Workup

  1. temperaturecooled
  2. customquenched with saturated aqueous sodium bicarbonate
  3. concentrationconcentrated in vacuo
  4. extractionThe residue was extracted with ethyl acetate
  5. washthe organics washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customchromatographed (40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-539bf8e21bb748a887149b5da52701f0
Source dataset
uspto-grants-2001_02
Patent number
US06194454B1

Reaction notes

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