Water → 4-Pyridinecarbonitrile, 2-(hexylamino)-

HRID 748137Notes

Reaction equation

HRID 748137 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1.[CH2:10]([NH2:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].O>CN1CCCC1=O>[CH2:10]([NH:16][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][N:3]=1)[C:8]#[N:9])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 8102HexylamineHCID 5686382-Chloro-4-cyanopyridine

Product 1

HCID 229392754-Pyridinecarbonitrile, 2-(hexylamino)-Yield 46%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

2-Chloro-4-cyanopyridine (0.40 g, 2.9 mmol) was dissolved in N-methylpyrrolidone (2.0 ml), and hexylamine (1.15 ml, 8.7 mmol) was added thereto. The reaction mixture was stirred at 100° C. for 4 hrs, combined with water, extracted with ethyl acetate, washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to a silica gel (50 g) column chromatography, eluted with hexane-ethyl acetate (3:1, v/v) to give the titled compound (0.26 g, 46%).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washeluted with hexane-ethyl acetate (3:1

Sources & evidence

ORD record
ord-fb1fa2bc12784f9ab4b6340887285d47
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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