Dipropylamine → 2-(Dipropylamino)isonicotinonitrile

HRID 14174

Reaction equation

HRID 14174 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][N:9]=1)[C:5]#[N:6].[CH2:10]([NH:13][CH2:14][CH2:15][CH3:16])[CH2:11][CH3:12]>>[CH2:10]([N:13]([CH2:14][CH2:15][CH3:16])[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][N:9]=1)[C:5]#[N:6])[CH2:11][CH3:12]

Participants

3

Reactant 2

HCID 8902DipropylamineHCID 5686382-Chloro-4-cyanopyridine

Product 1

HCID 146408542-(Dipropylamino)isonicotinonitrile

Conditions

Temperature
100 °C

Procedure

2-Chloroisonicotinonitrile (1.0 g) and dipropylamine (10 mL) were placed in a sealed heavy wall tube and heated to 100° C. for 18 h. The mixture was removed from heat and cooled to room temperature. The dipropylamine was removed under reduced pressure and the residue chromatographed on silica gel using 2% ethyl acetate in hexanes as eluent to give 1.06 g of the title compound: MS (ESI+) for C12H17N3 m/z 204.1 (M+H)+.

Workup

  1. customThe mixture was removed
  2. temperaturefrom heat
  3. temperaturecooled to room temperature
  4. customThe dipropylamine was removed under reduced pressure
  5. customthe residue chromatographed on silica gel using 2% ethyl acetate in hexanes as eluent

Sources & evidence

ORD record
ord-8806db662bf2457fa8f1fc0dac0d23e5
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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