Benzaldehyde → 6-(2-Benzylidenehydrazinyl)-3-chloro-4-(pyrrolidin-1-yl)pyridazine

HRID 47228Notes

Reaction equation

HRID 47228 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][NH2:9])=[CH:4][C:3]=1[N:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[Na+]>Cl>[CH:15](=[N:9][NH:8][C:5]1[N:6]=[N:7][C:2]([Cl:1])=[C:3]([N:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)[CH:4]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 226099553-Chloro-6-hydrazinyl-4-(1-pyrrolidinyl)pyridazine

Product 1

HCID 739942816-(2-Benzylidenehydrazinyl)-3-chloro-4-(pyrrolidin-1-yl)pyridazineYield 73.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 6-chloro-5-(pyrrolidin-1-yl)pyridazin-3-ylhydrazine (14 g, 0.063 mol) in 0.1 N hydrochloric acid (600 ml) was added benzaldehyde (6.4 ml, 0.063 mol) dropwise at room temperature. The mixture was stirred at 60° C. for 15 min, yielding a thick slurry. The pH of the solvent was adjusted to ˜11 with 4 N aqueous sodium hydroxide solution, and the precipitate filtered off. The residue was washed with water, ethanol and diethyl ether, yielding the title compound as a white solid (14 g, 73%). 1H NMR (360 MHz, DMSO) δ1.93 (4H, m), 3.58 (4H, m), 6.57 (1H, s), 7.35 (1H, m), 7.39 (2H, m), 7.66 (2H, d, J=7.1 Hz), 8.06 (1H, s), 11.16 (1H, s). MS (ES+) m/e 302 [MH]+, 304 [MH]+.

Workup

  1. customyielding a thick slurry
  2. filtrationthe precipitate filtered off
  3. washThe residue was washed with water, ethanol and diethyl ether

Sources & evidence

ORD record
ord-b77ba0fc4444481a959b726514d70c30
Source dataset
uspto-grants-2004_03
Patent number
US06699859B1

Reaction notes

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