Sodium amide → 2-Amino-3-Phenyl-6-methylpyridine

HRID 363199Notes

Reaction equation

HRID 363199 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]=1

Participants

4

Reactant 2

HCID 24533Sodium amideHCID 767442-Methyl-5-phenylpyridine

Product 1

HCID 463146392-Amino-3-Phenyl-6-methylpyridine

Reagents, catalysts & solvents 1

HCID 7061N,N-DiethylanilineSolvent

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

  1. temperatureThe reaction was cooled
  2. customquenched with ice (100 g)
  3. extractionthe mixture extracted with EtOAc
  4. extractionThe organic extract
  5. washwas washed with brine (50 mL)
  6. dry with materialdried (MgSO4), silica gel (100 g)
  7. additionwas added
  8. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-32a3396c1d2b456c8dbc096b5c0cb0df
Source dataset
uspto-grants-1999_02
Patent number
US05872136

Reaction notes

Loading…