Sodium amide → 2-Amino-4-(4-methylphenyl)pyridine

HRID 352784Notes

Reaction equation

HRID 352784 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[NH2-:14].[Na+]>CN(C)C1C=CC=CC=1>[NH2:14][C:10]1[CH:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)[CH:13]=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 24533Sodium amideHCID 5981334-(4-Methylphenyl)pyridine

Product 1

HCID 137770672-Amino-4-(4-methylphenyl)pyridineYield 47%

Reagents, catalysts & solvents 1

HCID 949N,N-DimethylanilineSolvent

Conditions

Temperature
110 °C

Procedure

Under an argon gas, 4-(4-methylphenyl)pyridine (2.74 g) was dissolved in N,N-dimethylaniline (10 ml), followed by the addition of sodium amide (1.40 g) at room temperature. After the resulting mixture was stirred at 110° C. for 2 days, the reaction mixture was cooled to room temperature. Brown powder precipitated by the addition of water was collected by filtration. The powder was further purified by chromatography on a silica gel column (ethyl acetate:toluene=1:1). After concentration of the resulting fraction, hexane was added and powder thus precipitated was collected by filtration and dried, whereby the title compound (1.40 g, 47%) was obtained.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. customBrown powder precipitated by the addition of water
  3. filtrationwas collected by filtration
  4. customThe powder was further purified by chromatography on a silica gel column (ethyl acetate:toluene=1:1)
  5. additionAfter concentration of the resulting fraction, hexane was added
  6. custompowder thus precipitated
  7. filtrationwas collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-7074ad6c91c0423883e7e60a5d09f42a
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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