Pyridinium chloride → 8-Hydroxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 61848Notes

Reaction equation

Br[C:2]1[C:3]([C:24]#[N:25])=[CH:4][CH:5]=[C:6]2[C:14]=1[NH:13][C:12]1[C:11]([CH3:16])([CH3:15])[C:10]3[CH:17]=[C:18]([O:21]C)[CH:19]=[CH:20][C:9]=3[C:8](=[O:23])[C:7]2=1.Cl.N1C=CC=CC=1>O>[OH:21][C:18]1[CH:19]=[CH:20][C:9]2[C:8](=[O:23])[C:7]3[C:6]4[C:14](=[CH:2][C:3]([C:24]#[N:25])=[CH:4][CH:5]=4)[NH:13][C:12]=3[C:11]([CH3:15])([CH3:16])[C:10]=2[CH:17]=1

Participants

Conditions

Temperature: 160 °C

Procedure

4-Bromo-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound U5, 325 mg, 0.822 mmol) was added with pyridine hydrochloride salt (3.80 g, 32.89 mmol) and stirred at 160° C. for 28 hr. The reaction solution was poured into water, extracted with ethyl acetate, washed with water, dried over sodium sulfate, and filtered. After concentration under reduced pressure, the title compound was obtained as a crude product.

Workup

extractionextracted with ethyl acetate
washwashed with water
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationAfter concentration under reduced pressure

Sources & evidence

ORD record: ord-2840a4f1a4cc4a9e9e561fbab4d3bb39
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440922B2

Reaction notes

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