HCID 3529665, compound → HCID 15887620, compound

HRID 377109Notes

Reaction equation

HRID 377109 reaction equation
[CH:1]1([N:7]([CH3:17])[C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)C.[OH-].[OH-].[Pd+2]>[CH:1]1([N:7]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][N:9]=2)[CH3:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 3529665HCID 3529665, compound

Product 1

HCID 15887620HCID 15887620, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Cyclohexyl-methyl-(5-nitro-pyridin-2-yl)-amine (1.72 g, 7.3 mmol) was dissolved in ethanol (80 mL) and treated with 20% palladium hydroxide on carbon (Pearlman's catalyst, 0.5 g) and the mixture was shaken under a hydrogen atmosphere (50 psi) for 6 hours. The catalyst was removed by filtration through celite then the filtrate was concentrated in vacuo and the resultant oil was chromatographed on SiO2 using 1:1 ethyl acetate/hexanes as eluent. MS (m/z): 206 (M+H)+ ; C12H19N3 requires 205.3.

Workup

  1. customThe catalyst was removed by filtration through celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customthe resultant oil was chromatographed on SiO2 using 1:1 ethyl acetate/hexanes as eluent

Sources & evidence

ORD record
ord-9285df38dbf5433680c04d97db0c75a2
Source dataset
uspto-grants-2000_02
Patent number
US06022884

Reaction notes

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