5-(1-Methyl-propenyl)-pyridin-2-ylamine → 5-Sec-butyl-pyridin-2-ylamine

HRID 1920728Notes

Reaction equation

HRID 1920728 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[CH:7][C:8]([NH2:11])=[N:9][CH:10]=1)=[CH:3][CH3:4]>C(O)C.[Pd]>[CH:2]([C:5]1[CH:6]=[CH:7][C:8]([NH2:11])=[N:9][CH:10]=1)([CH2:3][CH3:4])[CH3:1]

Participants

4

Reactant 1

HCID 674932645-(1-Methyl-propenyl)-pyridin-2-ylamine

Product 1

HCID 206746695-Sec-butyl-pyridin-2-ylamineYield 68.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 130 mg (0.87 mmol) of 5-(1-methyl-propenyl)-pyridin-2-ylamine in ethanol (5 mL) was reduced over palladium on charcoal (10 wt %, 13 mg) under a hydrogen atmosphere at room temperature for 18 h. The catalyst was separated by filtration through Celite® and washed with ethanol (5 mL). The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica, eluent ethyl acetate) to afford 90 mg of 5-sec-butyl-pyridin-2-ylamine. ES−MS: m/z 151 [M+H+];

Workup

  1. customThe catalyst was separated by filtration through Celite®
  2. washwashed with ethanol (5 mL)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography (silica, eluent ethyl acetate)

Sources & evidence

ORD record
ord-32c8816a16184fce9443a6da2dc64478
Source dataset
uspto-grants-2012_05
Patent number
US08173638B2

Reaction notes

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