Water → 5-(2,4-Dichloro-phenyl)-2-hydrazino-isonicotinonitrile

HRID 420500Notes

Reaction equation

HRID 420500 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:7]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])=[CH:8][N:9]=1)[C:5]#[N:6].O.[NH2:19][NH2:20].O>O1CCOCC1>[Cl:17][C:11]1[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:10]=1[C:7]1[C:4]([C:5]#[N:6])=[CH:3][C:2]([NH:19][NH2:20])=[N:9][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 451233412-Chloro-5-(2,4-dichloro-phenyl)-isonicotinonitrile

Product 1

HCID 666590105-(2,4-Dichloro-phenyl)-2-hydrazino-isonicotinonitrileYield 116.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-chloro-5-(2,4-dichloro-phenyl)-isonicotinonitrile (453 mg, 1.6 mmol) and hydrazine monohydrate (7.76 mL, 160 mmol) in dioxane (9 mL) was heated at 90° C. and stirred for 14 h. The reaction mixture was cooled to RT, poured into water (50 mL) and extracted with AcOEt (3×25 mL). The combined organic fractions were dried over Na2SO4, filtered, and evaporated to provide the crude title compound (520 mg, quant.) as a yellow solid, which was used without further purification. MS: 279 [M+1]+; HPLC: AtRet=1.44.

Workup

  1. extractionextracted with AcOEt (3×25 mL)
  2. dry with materialThe combined organic fractions were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-de19aca65dd54e01a05661103eecd455
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

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