Benzaldehyde → N-Benzylidene-N'-[6-chloro-5-(3,6-dihydro-2H-pyridin-1-yl)pyridazin-3-yl]hydrazine

HRID 429744Notes

Reaction equation

HRID 429744 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[CH2:15][CH:14]=[CH:13][CH2:12][CH2:11]1.[CH:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>Cl.O>[CH:16](=[N:9][NH:8][C:5]1[N:6]=[N:7][C:2]([Cl:1])=[C:3]([N:10]2[CH2:11][CH:12]=[CH:13][CH2:14][CH2:15]2)[CH:4]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 240BenzaldehydeHCID 18353340[6-chloro-5-(3,6-dihydro-2H-pyridin-1-yl)-pyridazin-3-yl]hydrazine

Product 1

HCID 73431615N-Benzylidene-N'-[6-chloro-5-(3,6-dihydro-2H-pyridin-1-yl)pyridazin-3-yl]hydrazineYield 90%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of [6-chloro-5-(3,6-dihydro-2H-pyridin-1-yl)-pyridazin-3-yl]hydrazine (1.0 g) in 0.1 M HCl (40 ml) at room temperature was added benzaldehyde (1.05 eq.). The mixture was heated at 50° C. for 2 hours then allowed to cool, diluted with water (100 ml) and filtered. The resulting solid was dried in vacuo, and isolated as a yellow solid (1.25 g, 90%). 1H NMR (250 MHz, CDCl3) 11.65 (1H, br s), 8.31 (1H, s), 7.73 (2H, m), 7.38 (2H, m), 7.04 (1H, s), 5.97 (1H, m), 5.83 (1H, m), 3.80 (2H, m), 3.54 (2H, m), 2.40 (2H, m). MS (ES+) 314 [MH]+, 316 [MH]+.

Workup

  1. temperatureto cool
  2. filtrationfiltered
  3. customThe resulting solid was dried in vacuo

Sources & evidence

ORD record
ord-e567f229f58144308d997a4ffb8aa625
Source dataset
uspto-grants-2001_11
Patent number
US06319924B1

Reaction notes

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