2-Hydrazinopyridine → 8-Methoxy-10,10-dimethyl-10,11-dihydro-5H-1,11-diaza-benzo[B]fluorene

HRID 61794

Reaction equation

[NH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)N.[CH3:9][O:10][C:11]1[CH:20]=[C:19]2[C:14]([CH2:15][CH2:16][C:17](=O)[C:18]2([CH3:22])[CH3:21])=[CH:13][CH:12]=1>CN1C(=O)CCC1.C(OCC)(=O)C>[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]2[CH2:15][C:16]3[C:8]4[CH:7]=[CH:6][CH:5]=[N:4][C:3]=4[NH:1][C:17]=3[C:18]([CH3:21])([CH3:22])[C:19]=2[CH:20]=1

Participants

Conditions

Temperature: 190 °C

Procedure

2-Hydrazinopyridine (1.3 g, 11.8 mmol) and 7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one (Compound A2, 2.4 g, 11.8 mmol) were dissolved in NMP (60 mL), and stirred at 190° C. for 48 hr. The reaction solution was diluted with ethyl acetate, washed with water and dried over magnesium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the target compound (white solid, 101 mg, 3%).

Workup

washwashed with water
dry with materialdried over magnesium sulfate
customThe drying agent was removed by filtration
customthe residues obtained
concentrationafter concentration under reduced pressure
customwere purified by silica gel column chromatography (hexane/ethyl acetate)
customto obtain the target compound (white solid, 101 mg, 3%)

Sources & evidence

ORD record: ord-d2cfd862385d4e1bbadc5347e9025ed2
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440922B2

Linked notes

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