HCID 86718524, compound → HCID 43566121, compound

HRID 929938Notes

Reaction equation

HRID 929938 reaction equation
[N+:1]([CH:4]([CH2:13][CH3:14])[CH:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[OH:6])([O-])=O>C(O)C.[Ni]>[NH2:1][CH:4]([CH2:13][CH3:14])[CH:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[OH:6]

Participants

4

Reactant 1

HCID 86718524HCID 86718524, compound

Product 1

HCID 43566121HCID 43566121, compoundYield 24.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-nitro-1-pyridin-3-yl-butan-1-ol (1.0 g, 4.44 mmol) in ethanol (20 mL) was purged with argon, and 100 mg of Raney-Nickel was added at room temperature. The reaction mixture was three times evacuated and refilled with hydrogen. The reaction was stirred for 16 hours at room temperature. Raney-Nickel was then filtered over Hyflo, and the Hyflo washed with EtOH. The filtrate was then concentrated. The residue was purified by column chromatography (40 g of SiO2) using MeOH in CH2Cl2 from 0% to 100% in order to give the title compound as a yellow oil (180 mg, 21%). LC-MS: [M+H] 167.1; Rt 0.21 min; (LCMS method 1).

Workup

  1. additionwas added at room temperature
  2. customevacuated
  3. additionrefilled with hydrogen
  4. filtrationRaney-Nickel was then filtered over Hyflo
  5. washthe Hyflo washed with EtOH
  6. concentrationThe filtrate was then concentrated
  7. customThe residue was purified by column chromatography (40 g of SiO2)

Sources & evidence

ORD record
ord-1e32823de61347d69b4b724152b65a06
Source dataset
uspto-grants-2016_03
Patent number
US09296733B2

Reaction notes

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