Ammonia → 2-Amino-5-(4-chlorophenyl)pyridine-3-carbonitrile

HRID 1980305Notes

Reaction equation

HRID 1980305 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:4][N:3]=1.[NH3:17]>CS(C)=O>[NH2:17][C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 27640422-Chloro-5-(4-chlorophenyl)nicotinonitrile

Product 1

HCID 132426422-Amino-5-(4-chlorophenyl)pyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 2-chloro-5-(4-chlorophenyl)-3-pyridinecarbonitrile (2.0 grams) in 30 ml DMSO was heated in an oil bath at 80°-90° C. and then treated with gaseous NH3 for 21/2 hours. The reaction mixture was allowed to stand at room temperature for about 60 hours and then additional starting material (4 g) in 35 ml DMSO was added. The mixture was then treated with NH3 at 80°-90° C. for about 28 hours and poured into ice water. The tan solid precipitate which formed was filtered and used without further purification, yield 5.5 grams, m.p. 202°-204° C.

Workup

  1. customThe tan solid precipitate which formed
  2. filtrationwas filtered
  3. customused without further purification, yield 5.5 grams, m.p. 202°-204° C.

Sources & evidence

ORD record
ord-9f15f1a1a74f49cf97dff05bffac1faf
Source dataset
uspto-grants-1985_04
Patent number
US04508722

Reaction notes

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