6-chloro-N-(3-chlorophenyl)pyridazin-3-amine → N-(3-chlorophenyl)-6-hydrazinylpyridazin-3-amine

HRID 446898Notes

Reaction equation

HRID 446898 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)=[CH:4][CH:3]=1.C(O)COCCOCCO.O.[NH2:27][NH2:28]>O>[Cl:15][C:11]1[CH:10]=[C:9]([NH:8][C:5]2[N:6]=[N:7][C:2]([NH:27][NH2:28])=[CH:3][CH:4]=2)[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 430902446-chloro-N-(3-chlorophenyl)pyridazin-3-amineHCID 86642294Triethylene glycol hydrazine hydrate

Product 1

HCID 59363292N-(3-chlorophenyl)-6-hydrazinylpyridazin-3-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(Step 1-ii) 6-chloro-N-(3-chlorophenyl)pyridazin-3-amine (88.1 g, 367 mmol) was suspended in 1:6 triethylene glycol/hydrazine hydrate and heated to reflux for 4 hours. The reaction mixture was cooled to room temperature, diluted with water and a solid filtered off. This solid was triturated with Et2O to give the product, N-(3-chlorophenyl)-6-hydrazinylpyridazin-3-amine, as a brown solid (60 g, 254 mmol, 69% yield): 1H NMR (500 MHz, DMSO-d6) 9.23 (s, 1H), 8.09 (t, J=1.8 Hz, 1H), 7.46 (d, J=8.2 Hz, 1H), 7.24 (t, J=8.1 Hz, 1H), 7.08 (d, J=9.4 Hz, 1H), 7.00 (d, J=9.4 Hz, 1H), 6.85 (dd, J=1.3, 7.8 Hz, 1H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 hours
  3. filtrationa solid filtered off
  4. customThis solid was triturated with Et2O

Sources & evidence

ORD record
ord-bb5d3d66d0a44216a04eaa2ec42dc640
Source dataset
uspto-grants-2013_07
Patent number
US08481538B2

Reaction notes

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