Ammonia → 2-Amino-4,6-dimethyl-5-phenylpyridine-3-carbonitrile

HRID 1980316Notes

Reaction equation

HRID 1980316 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:4]([CH3:17])[N:3]=1.[NH3:18]>CS(C)=O>[NH2:18][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:4]([CH3:17])[N:3]=1

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 135028532-Chloro-4,6-dimethyl-5-phenylpyridine-3-carbonitrile

Product 1

HCID 204025382-Amino-4,6-dimethyl-5-phenylpyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-Chloro-4,6-dimethyl-5-phenyl-3-pyridinecarbonitrile (8.3 grams) was dissolved in 110 ml DMSO and treated with gaseous NH3 at a temperature of 100°-110° C. After about 66 hours of heating and treatment with NH3, the reaction mixture was cooled and poured into ice water. A solid precipitate formed which was collected, washed with water, and then dried in an oven desicator. The identity of the desired product was confirmed by NMR.

Workup

  1. temperatureAfter about 66 hours of heating
  2. customA solid precipitate formed which
  3. customwas collected
  4. washwashed with water
  5. customdried in an oven desicator

Sources & evidence

ORD record
ord-4e8689eb7dbe45b1b3678dccde416c11
Source dataset
uspto-grants-1985_04
Patent number
US04508722

Reaction notes

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