Methanol → HCID 22219492, compound

HRID 1793935Notes

Reaction equation

HRID 1793935 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#[N:12])=[C:6]([N+:13]([O-:15])=[O:14])[CH:5]=1)([CH3:3])[CH3:2].CO.O>O1CCCC1>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][NH2:12])=[C:6]([N+:13]([O-:15])=[O:14])[CH:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 22219471HCID 22219471, compound

Product 1

HCID 22219492HCID 22219492, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 0.154 g of (4-isopropyl-2-nitrophenyl)acetonitrile in 2 mL of tetrahydrofuran was added 1.62 mL of 0.93 mol/L borane-tetrahydrofuran complex under ice-cooling, and the mixture was stirred at room temperature for 15 hours. The reaction mixture was cooled under ice-cooling, and to the mixture were added 2 mL of methanol and 20 mL of water. After the mixture was extracted with ethyl acetate, the organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on aminopropylated silica gel (eluent: ethyl acetate) to give 64 mg of 2-(4-isopropyl-2-nitrophenyl)ethylamine.

Workup

  1. temperaturecooling
  2. temperatureThe reaction mixture was cooled under ice-
  3. temperaturecooling
  4. extractionAfter the mixture was extracted with ethyl acetate
  5. washthe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by column chromatography on aminopropylated silica gel (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-2e1e7a8ae882485281f97a4021a44abb
Source dataset
uspto-grants-2006_04
Patent number
US07022689B2

Reaction notes

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