Ammonium Hydroxide → 2-Chloro-5-(4-chlorophenyl)nicotinonitrile

HRID 1980304Notes

Reaction equation

[C:1]([C:3]1[C:4](=O)[NH:5][CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH:8]=1)#[N:2].C1(P(Cl)([Cl:25])=O)C=CC=CC=1.[NH4+].[OH-]>>[Cl:25][C:4]1[C:3]([C:1]#[N:2])=[CH:8][C:7]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:6][N:5]=1

Participants

Reactant 3

HCID 14923Ammonium Hydroxide

HCID 69990Phenylphosphonic dichloride

HCID 27639105-(4-Chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

Product 1

HCID 27640422-Chloro-5-(4-chlorophenyl)nicotinonitrile

Conditions

Temperature: 175 °C

Procedure

A mixture of 3-cyano-5-(4-chlorophenyl)-2-(1H)-pyridone (2.0 grams) and phenylphosphonic dichloride (3.8 grams) was heated for 4 hours at 175° C. in an oil bath. The mixture was poured into ice water and was made alkaline by stirring with NH4OH. The resulting brownish solid product was used without further purification, yield 2.0 g., m.p. 185°-187° C.

Workup

customThe resulting brownish solid product was used without further purification, yield 2.0 g

Sources & evidence

ORD record: ord-5c5c083954fb44d9ad377616b7a0b810
Source dataset: uspto-grants-1985_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04508722

Reaction notes

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