Hydrazine hydrate (1:1) → 3-Benzyl-6-bromo-8-methyl-2,3,4,9-tetrahydro-1H-3-aza-fluorene

HRID 1714155Notes

Reaction equation

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

Participants

Conditions

Temperature: 180 °C

Procedure

To a solution of cis-3-benzyl-6-bromo-8-methyl-1,2,3,4,4a,9a-hexahydro-3-aza-fluoren-9-one (680 mg, 1.8 mmol) in ethylene glycol (9.0 mL) was added hydrazine hydrate (1.8 mL). The reaction mixture was heated at 120° C. for 2 h and at 180° C. for additional 15 h. The reaction was cooled to 20° C., quenched by addition of brine and extracted with CH2Cl2. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was chromatographed in silica gel column (hexane/EtOAc 9/1) to give the title compound (42 mg, 0.12 mmol): MS (ES) 354.1 (M+H).

Workup

temperatureThe reaction was cooled to 20° C.
customquenched by addition of brine
extractionextracted with CH2Cl2
washThe organic layer was washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was chromatographed in silica gel column (hexane/EtOAc 9/1)

Sources & evidence

ORD record: ord-21ea081d36724f47bf0a6a6beafd7d92
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795436B2

Reaction notes

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