5-(1-Methyl-propenyl)-pyridin-2-ylamine → 5-Sec-butyl-pyridin-2-ylamine
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
Product 1
Reagents, catalysts & solvents 2
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
- customThe catalyst was separated by filtration through Celite®
- washwashed with ethanol (5 mL)
- concentrationThe filtrate was concentrated under reduced pressure
- 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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