Hydrazine hydrate (1:1) → 4-(4-chloro-3-methylphenyl)-1H-pyrazole-3,5-diamine

HRID 1912899Notes

Reaction equation

HRID 1912899 reaction equation
O.[NH2:2][NH2:3].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:14]#[N:15])[C:12]#[N:13])=[CH:7][C:6]=1[CH3:16]>C(Cl)(Cl)Cl>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:14]([NH2:15])=[N:2][NH:3][C:12]=2[NH2:13])=[CH:7][C:6]=1[CH3:16]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 866651792-(4-Chloro-3-methylphenyl)malononitrile

Product 1

HCID 687511524-(4-chloro-3-methylphenyl)-1H-pyrazole-3,5-diamine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

Hydrazine monohydrate (0.312 mL, 6.4 mmol) was added to a solution of the product from Example 47A (512 mg, 2.69 mmol) in CHCl3 (25 mL). The reaction flask was evacuated and purged with nitrogen (3 cycles) and the mixture was heated at 70° C. under nitrogen for 22 hours, then cooled to room temperature. The mixture was concentrated under vacuum to provide the title compound as a beige solid. MS (DCI/NH3) m/z 223/225 (M+H)+.

Workup

  1. customThe reaction flask was evacuated
  2. custompurged with nitrogen (3 cycles)
  3. temperaturecooled to room temperature
  4. concentrationThe mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-a4e073b01ed3423fab9e38b75e8a600e
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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