6-Amino-3-chloropyridazine → [2-(6-Chloro-3-pyridazinyl)-2-azavinyl]dimethylamine

Reaction equation

[NH2:1][C:2]1[N:3]=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.CO[CH:11](OC)[N:12]([CH3:14])[CH3:13]>>[Cl:8][C:5]1[N:4]=[N:3][C:2]([N:1]=[CH:11][N:12]([CH3:14])[CH3:13])=[CH:7][CH:6]=1

Participants

Reactant 2

HCID 216436-Amino-3-chloropyridazine

HCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 6802247[2-(6-Chloro-3-pyridazinyl)-2-azavinyl]dimethylamine

Procedure

A mixture of 3-amino-6-chloropyridazine (6.39 g, 49.3 mmol) and N,N-dimethylformamide dimethyl acetal (7.67 mL, 54.3 mmol) was stirred under reflux for 75 min. Excess N,N-dimethyl-formamide dimethyl acetal was removed to afford the title compound as a beige solid (tR 1.0 min (conditions 1), MH+=185).

Workup

temperatureunder reflux for 75 min
customExcess N,N-dimethyl-formamide dimethyl acetal was removed

Sources & evidence

ORD record: ord-b23567cd310b4b37811b6c274507ad7a
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822468B2

Reaction notes

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