Acetic Acid → 2,3-Dichloro-8-methoxy-6,6-dimethyl-6,11-dihydro-5H-benzo[b]carbazole

HRID 61861Notes

Reaction equation

C(O)(=O)C.[CH3:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][C:13](=O)[C:14]2([CH3:18])[CH3:17])=[CH:9][CH:8]=1.Cl.[Cl:21][C:22]1[CH:23]=[C:24]([NH:29]N)[CH:25]=[CH:26][C:27]=1[Cl:28].C(OCC)C>O>[Cl:28][C:27]1[CH:26]=[C:25]2[C:24](=[CH:23][C:22]=1[Cl:21])[NH:29][C:13]1[C:14]([CH3:18])([CH3:17])[C:15]3[CH:16]=[C:7]([O:6][CH3:5])[CH:8]=[CH:9][C:10]=3[CH2:11][C:12]2=1

Participants

Conditions

Temperature: 90 °C

Procedure

Under nitrogen atmosphere, the acetic acid (1 mL) suspension of 7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one (Compound A2, 92.3 mg, 0.452 mmol) and (3,4-dichlorophenyl)hydrazine hydrochloric acid salt (Compound Y1, 96.5 mg, 0.452 mmol) was stirred at ambient temperature of 90° C. for 3.5 hr. After cooling to room temperature, the reaction mixture was added with diethyl ether and water, and the resulting mixture was extracted twice with diethyl ether. The organic layer was washed three times with water, dried over sodium sulfate, and concentrated under reduced pressure. The resulting crude product was purified by flash column chromatography {Merck Kieselgel60, solution for elution:hexane/ethyl acetate (4:1)} to obtain the title compound (pale yellow solid, 62.1 mg, 40%).

Workup

temperatureAfter cooling to room temperature
extractionthe resulting mixture was extracted twice with diethyl ether
washThe organic layer was washed three times with water
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe resulting crude product was purified by flash column chromatography {Merck Kieselgel60, solution for elution

Sources & evidence

ORD record: ord-f14c87bdc81246249a84c3e40148328a
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440922B2

Reaction notes

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