Ethyl Acetate → 2,3-Dichloro-8-hydroxy-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one

HRID 61863

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][C:14]=1[Cl:15])[NH:11][C:10]1[C:9]([CH3:17])([CH3:16])[C:8]3[CH:18]=[C:19]([O:22]C)[CH:20]=[CH:21][C:7]=3[C:6](=[O:24])[C:5]2=1.[Cl-].[NH+]1C=CC=CC=1.C(OCC)(=O)C>O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][C:14]=1[Cl:15])[NH:11][C:10]1[C:9]([CH3:17])([CH3:16])[C:8]3[CH:18]=[C:19]([OH:22])[CH:20]=[CH:21][C:7]=3[C:6](=[O:24])[C:5]2=1

Participants

Conditions

Temperature: 160 °C

Procedure

Mixture of 2,3-dichloro-8-methoxy-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one (Compound Y3, 16.5 mg, 0.0457 mmol) and pyridinium chloride (0.2 g) was stirred at ambient temperature of 160° C. for 7 hr. The reaction mixture was cooled to room temperature and added with ethyl acetate and water. The mixture was extracted three times with ethyl acetate. The organic layer was washed twice with water, dried over sodium sulfate, and concentrated under reduced pressure. The resulting crude product was used for the next step without further purification (brown solid, 14.8 mg, 94%).

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionThe mixture was extracted three times with ethyl acetate
washThe organic layer was washed twice with water
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe resulting crude product was used for the next step without further purification (brown solid, 14.8 mg, 94%)

Sources & evidence

ORD record: ord-c23d8becc1b5464fac70565077e5f0e9
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440922B2

Linked notes

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