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

HRID 1980304
Notes
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Reaction equation

HRID 1980304 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 69990Phenylphosphonic dichlorideHCID 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

  1. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes