Phenylphosphonic dichloride → 2-Chloro-6-(4-chlorophenyl)nicotinonitrile

HRID 1980327Notes

Reaction equation

HRID 1980327 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:13][C:12](=O)[C:11]([C:15]#[N:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C1(P(Cl)([Cl:25])=O)C=CC=CC=1>>[Cl:25][C:12]1[C:11]([C:15]#[N:16])=[CH:10][CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:13]=1

Participants

3

Reactant 2

HCID 69990Phenylphosphonic dichlorideHCID 2741320HCID 2741320, compound

Product 1

HCID 27652332-Chloro-6-(4-chlorophenyl)nicotinonitrile

Procedure

6-(4-Chlorophenyl)-3-cyano-2-pyridone (42 grams) and phenylphosphonic dichloride were heated for 2.5 hours at 175°-180° C. taking precautions to keep the reaction dry. Upon cooling, the reaction mixture was poured into 500 ml of ice water and was made slightly alkaline by the addition of concentrated NH4OH. A solid product formed which was thoroughly washed with water and recrystallized from ethanol/DMF, yield 42 grams, m.p. 179°-181° C.

Workup

  1. customdry
  2. temperatureUpon cooling
  3. additionthe reaction mixture was poured into 500 ml of ice water
  4. additionwas made slightly alkaline by the addition of concentrated NH4OH
  5. customA solid product formed which
  6. washwas thoroughly washed with water
  7. customrecrystallized from ethanol/DMF, yield 42 grams, m.p. 179°-181° C.

Sources & evidence

ORD record
ord-2e206ddcd6bf492bb622c125f45d7c62
Source dataset
uspto-grants-1985_04
Patent number
US04508722

Reaction notes

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