2-Hydrazinopyridine → 3,6,6-Trimethyl-1-pyridin-2-yl-5,7-dihydroindazol-4-one

HRID 2084281Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-acetyl-5,5-dimethyl-cyclohexane-1,3-dione (0.5 g, 2.75 mmol), prepared as described in example 2, and 2-hydrazino-pyridine (0.3 g, 2.75 mmol) in ethanol (15 ml) was stirred at 80° C. for 4 hours. After evaporation of the solvent, the residue was chromatographed on silica gel (cyclohexane:ethyl acetate=10:20). The title compound was obtained as a colourless solid (0.5 g, 73%): m.p. 122-123° C.

Workup

customprepared
customAfter evaporation of the solvent
customthe residue was chromatographed on silica gel (cyclohexane:ethyl acetate=10:20)

Sources & evidence

ORD record: ord-d8cc340f85254eef9c1abd5888faae67
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06716856B1

Reaction notes

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