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

HRID 1995601Notes

Reaction equation

HRID 1995601 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-ae742209663f435aad0a723c2cd9d960
Source dataset
uspto-grants-1983_09
Patent number
US04405552

Reaction notes

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