Ammonia → 2-Amino-3-cyanopyridine

HRID 647757Notes

Reaction equation

HRID 647757 reaction equation
C[N:2](C)[CH:3]=[CH:4][CH:5]=[C:6]([C:9]#[N:10])[C:7]#[N:8].N>CO>[NH2:10][C:9]1[N:2]=[CH:3][CH:4]=[CH:5][C:6]=1[C:7]#[N:8]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 53731931[3-(Dimethylamino)prop-2-en-1-ylidene]propanedinitrile

Product 1

HCID 8182592-Amino-3-cyanopyridineYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

17.3 parts of 4-dimethylamino-1,1-dicyano-1,3-butadiene and 90 parts of methanol are combined in a stirred autoclave. 16 parts of liquid ammonia are added and the mixture is stirred at 150° C. for 3 hours. The mixture is evaporated down under reduced pressure and, after the addition of ethanol, the precipitate is filtered off with suction and dried. 12.7 parts (91% of theory) of 2-aminonicotine nitrile, of melting point 130° to 132° C. (from ethanol), are obtained.

Workup

  1. customThe mixture is evaporated down under reduced pressure
  2. additionafter the addition of ethanol
  3. filtrationthe precipitate is filtered off with suction
  4. customdried

Sources & evidence

ORD record
ord-81e79ce1d36c461d9f3eba0e4c094722
Source dataset
uspto-grants-1983_10
Patent number
US04410465

Reaction notes

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