Methylhydrazine → 2,3-Dihydro-2-methyl-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyridazin-1,4(6H)-dione

HRID 1835151Notes

Reaction equation

[CH3:1][NH:2][NH2:3].[C:4]1([CH2:14][N:15]2[CH:19]=[C:18]([C:20](OCC)=[O:21])[C:17]([C:25](OCC)=[O:26])=[CH:16]2)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1>C(O)C>[CH3:1][N:2]1[C:25](=[O:26])[C:17]2=[CH:16][N:15]([CH2:14][C:4]3[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[CH:7]=[CH:6][CH:5]=3)[CH:19]=[C:18]2[C:20](=[O:21])[NH:3]1

Participants

Conditions

Temperature: 200 °C

Procedure

Methyl hydrazine (0.55 ml) was added to a solution of diethyl 1-(1-naphthalenylmethyl)pyrrole-3,4-dicarboxylate (1.00 g) in ethanol (10 ml). The mixture was heated at 200° C. in a sealed tube for 3 days. The mixture was evaporated and the residue was purified by column chromatography, eluting with ethyl acetate:methanol (19:1). The resulting solid was suspended in ethyl acetate (25 ml), heated to reflux, and allowed to cool to ambient temperature. The title compound (0.105 g) was collected by filtration.

Workup

customThe mixture was evaporated
customthe residue was purified by column chromatography
washeluting with ethyl acetate:methanol (19:1)
temperatureheated
temperatureto reflux
temperatureto cool to ambient temperature
filtrationThe title compound (0.105 g) was collected by filtration

Sources & evidence

ORD record: ord-d616436f19a0493ab55b9218d141bc9f
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06770646B2

Reaction notes

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