Sodium amide → 2-Amino-3-Phenyl-6-methylpyridine
Reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2-:14].[Na+]>CCN(C1C=CC=CC=1)CC>[NH2:14][C:8]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:12][CH:11]=[C:10]([CH3:13])[N:9]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 3-phenyl-6-methyl pyridine (0.815 g, 4.82 mmol), and sodium amide (752 mg, 19.3 mmol) in diethylaniline (10 mL) was heated at 180° C. for 72 hours. The reaction was cooled and quenched with ice (100 g), and the mixture extracted with EtOAc. The organic extract was washed with brine (50 mL), dried (MgSO4), silica gel (100 g) was added and the solvent evaporated in vacuo.
Workup
- temperatureThe reaction was cooled
- customquenched with ice (100 g)
- extractionthe mixture extracted with EtOAc
- extractionThe organic extract
- washwas washed with brine (50 mL)
- dry with materialdried (MgSO4), silica gel (100 g)
- additionwas added
- customthe solvent evaporated in vacuo
Sources & evidence
- ORD record
- ord-32a3396c1d2b456c8dbc096b5c0cb0df
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05872136
Reaction notes
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