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

HRID 2054378Notes

Reaction equation

HRID 2054378 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([CH2:6][C:7]#[N:8])=O.O.[NH2:14][NH2:15]>C(O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]1[CH:6]=[C:7]([NH2:8])[NH:14][N:15]=1

Participants

5

Reactant 2

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

Product 1

HCID 178507276HCID 178507276, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 2-chlorobenzoylacetonitrile (400 g, 2.23 mol) in ethanol (9 L) was added hydrazine hydrate (221 g, 4.42 mol) over 15 minutes while maintaining internal reaction temperature at 15 to 25° C. The mixture was then heated at 75° C. for 20 hr. After cooling, the reaction was concentrated, in vacuo, to give a brown oil. The residue was dissolved in ethyl acetate (4 L), washed with half saturated brine (4 L), and then dried (Na2SO4) to a give a crude, dark orange solution of 5-(2-chlorophenyl)-2H-pyrazol-3-ylamine that was carried directly into the next reaciton: +ESI MS (M+1) 194.0.

Workup

  1. temperatureThe mixture was then heated at 75° C. for 20 hr
  2. temperatureAfter cooling
  3. concentrationthe reaction was concentrated, in vacuo
  4. customto give a brown oil
  5. washwashed with half saturated brine (4 L)
  6. dry with materialdried (Na2SO4) to

Sources & evidence

ORD record
ord-08bc32e190174e57beac16432648561b
Source dataset
uspto-grants-2008_02
Patent number
US07329658B2

Reaction notes

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