2,5-Hexanedione → N-(2,5-Dimethylpyrrol-1-yl)-6-(4-methylpiperazin-1-yl)pyridazin-3-amine

HRID 1390003Notes

Reaction equation

[NH:1]([C:3]1[N:4]=[N:5][C:6]([N:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)=[CH:7][CH:8]=1)[NH2:2].[CH3:16][C:17](=O)[CH2:18][CH2:19][C:20](=O)[CH3:21]>C(O)(=O)C>[CH3:21][C:20]1[N:2]([NH:1][C:3]2[N:4]=[N:5][C:6]([N:9]3[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]3)=[CH:7][CH:8]=2)[C:17]([CH3:16])=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 7 g (35 m moles) of 3-hydrazino-6-(4-methyl-1-piperazinyl)-pyridazine and 4.1 g (36 m moles) of 2,5-hexanedione in 100 ml of acetic acid is heated for 3 hours at 70° C. The solvent is evaporated off under vacuum and the oily residue is dissolved in water and made alkaline with 10% sodium hydroxyde. The mixture is extracted with ethyl acetate and the organic layer is evaporated to dryness in vacuo. The solid residue is crystallized first from ethyl ether and then from ethyl acetate yielding 2.6 g (26%) of the product of the title which melts at 181°-182° C.

Workup

customThe solvent is evaporated off under vacuum
dissolutionthe oily residue is dissolved in water
extractionThe mixture is extracted with ethyl acetate
customthe organic layer is evaporated to dryness in vacuo
customThe solid residue is crystallized first from ethyl ether

Sources & evidence

ORD record: ord-1ed09182a629421385e573f67784e038
Source dataset: uspto-grants-1981_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04247551

Reaction notes

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