Hydrazine hydrate (1:1) → 6-(4-Aminophenyl)-2-chloronicotinonitrile

HRID 556441Notes

Reaction equation

HRID 556441 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([NH:14]C(NC3C=C(C(F)(F)F)C=CC=3F)=O)=[CH:10][CH:9]=2)[CH:5]=[CH:4][C:3]=1[C:29]#[N:30].O.NN>C(O)CC>[NH2:14][C:11]1[CH:10]=[CH:9][C:8]([C:6]2[CH:5]=[CH:4][C:3]([C:29]#[N:30])=[C:2]([Cl:1])[N:7]=2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 597666741-[4-(6-Chloro-5-cyanopyridin-2-yl)phenyl]-3-(2-fluoro-5-trifluoromethylphenyl)urea

Product 1

HCID 597666616-(4-Aminophenyl)-2-chloronicotinonitrileYield 132.5%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Conditions

Temperature
80 °C

Procedure

0.46 mmol (200 mg) of 1-[4-(6-chloro-5-cyanopyridin-2-yl)phenyl]-3-(2-fluoro-5-trifluoromethylphenyl)urea is suspended in 3.2 ml of 1-propanol. 0.13 ml (0.14 g, 2.76 mmol, 6 eq.) of hydrazine hydrate is added. The suspension is heated at 80° C. for 10 h. The mixture is filtered and the solid is dried so as to obtain 140 mg of the expected product.

Workup

  1. filtrationThe mixture is filtered
  2. customthe solid is dried so as

Sources & evidence

ORD record
ord-986e30c2e0d745e8b334f0d8b37bd24d
Source dataset
uspto-grants-2011_11
Patent number
US08058290B2

Reaction notes

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