Hydrazine hydrate (1:1) → HCID 178507276, compound

HRID 1452768

Reaction equation

HRID 1452768 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[CH2:9][C:10]#[N:11].O.[NH2:14][NH2:15]>C(O)C>[NH2:11][C:10]1[NH:15][N:14]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[CH:9]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 27342012-Chlorobenzoylacetonitrile

Product 1

HCID 178507276HCID 178507276, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-(chlorophenyl)-3-oxo-propionitrile (4.0 g, 22.2 mmol) in absolute ethanol (21 mL) was added hydrazine hydrate (6.5 mL, 134 mmol). The reaction mixture was stirred at 80° C. for 15 hours, then it was concentrated in vacuo and purified on silica gel with 0-10% MeOH in CH2Cl2 as eluent to give 3.8 g (87% yield) of 5-amino-3-(2-chlorophenyl)pyrazole as a yellow solid. 1H NMR (d6-DMSO) δ: 11.7 (broad s, 1H), 7.66 (d, 1H), 7.48 (d, 1H), 7.35 (t, 1H), 7.30 (t, 1H), 5.83 (s, 1H), 4.84 (broad s, 2H); HPLC/MS m/z: 194.1 [MH]+.

Workup

  1. concentrationit was concentrated in vacuo
  2. custompurified on silica gel with 0-10% MeOH in CH2Cl2 as eluent

Sources & evidence

ORD record
ord-4a18ad9ee1e041b895ca8bc2150a214b
Source dataset
uspto-grants-2009_01
Patent number
US07473783B2

Linked notes

Loading…