O-Xylene → 4-Propylpyridin-2-amine

HRID 487999

Reaction equation

HRID 487999 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)[CH2:2][CH3:3].[NH2-:10].[Na+].C1(C)C(C)=CC=CC=1>O>[NH2:10][C:6]1[CH:5]=[C:4]([CH2:1][CH2:2][CH3:3])[CH:9]=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 24533Sodium amide2×HCID 707384-Propylpyridine

Product 1

HCID 70225944-Propylpyridin-2-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

75 g (0.62M) of 4-n-propylpyridine and 28 g (0.73M) of sodium amide were added to 250 ml of xylene, and the mixture was heated under reflux for 10 hr. Water was added in small portions to the reaction mixture under ice cooling to decompose excess sodium amide, and the reaction mixture was extracted with ethyl acetate, dried over magnesium sulfate and then purified by column chromatography (dichloromethanemethanol 50:1→20:1). The yield was 33 g. (blackish purple solid)

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 10 hr
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. custompurified by column chromatography (dichloromethanemethanol 50:1→20:1)

Sources & evidence

ORD record
ord-99275caca2504d5a8f8480478f041851
Source dataset
uspto-grants-1994_03
Patent number
US05298518

Linked notes

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