HCID 66728944, compound → 5-(Propan-2-yl)pyridin-3-amine
Reaction equation
[CH2:1]=[C:2]([C:4]1[CH:5]=[C:6]([NH2:10])[CH:7]=[N:8][CH:9]=1)[CH3:3]>C(O)C.[Pd]>[CH:2]([C:4]1[CH:5]=[C:6]([NH2:10])[CH:7]=[N:8][CH:9]=1)([CH3:3])[CH3:1]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 5-(prop-1-en-2-yl)pyridin-3-amine (0.773 g, 2.48 mmol) in ethanol (8 mL) was added 10% Pd/C (0.132 g, 0.124 mmol) and the resulting suspension was stirred under a hydrogen atmosphere (1 atm) for 18 h. The reaction was filtered through Celite® and washed forward with EtOH. The filtrate was concentrated, diluted with EtOAc (30 mL) and washed with H2O (1×15 ml) and brine (1×15 ml). The aqueous phase was back-extracted with EtOAc (1×20 ml). The combined organic layers were dried (MgSO4) and concentrated to afford 5-isopropylpyridin-3-amine (0.453 g, 134%) as a light yellow oil. MS (ESI) m/z: 137.1 (M+H+).
Workup
- filtrationThe reaction was filtered through Celite®
- washwashed forward with EtOH
- concentrationThe filtrate was concentrated
- additiondiluted with EtOAc (30 mL)
- washwashed with H2O (1×15 ml) and brine (1×15 ml)
- extractionThe aqueous phase was back-extracted with EtOAc (1×20 ml)
- dry with materialThe combined organic layers were dried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-132e49140dad42fab7c464c6af402992
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08143293B2
Reaction notes
Loading…