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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2275155Generated: October 25, 2026

Sodium Bicarbonate → 9-Amino-6,6-dimethyl-8-(1-methyl-piperidin-4-yl oxy)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

https://huagongshe.com/reaction/2275155

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium BicarbonateHCID 516892—
ReactantAmmonium AcetateHCID 517165—
Reactant6,6-Dimethyl-8-(1-methyl-piperidin-4-yloxy)-9-nitro-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileHCID 66834432—
Catalysttitanium(III) trichlorideHCID 10313229—
SolventEthanolHCID 702—
Product9-Amino-6,6-dimethyl-8-(1-methyl-piperidin-4-yl oxy)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileHCID 6683438878%

Reaction Steps

6,6-Dimethyl-8-(1-methyl-piperidin-4-yloxy)-9-nitro-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound D1, 83 mg, 0.19 mmol) was dissolved in ethanol, added with aqueous solution of ammonium acetate and aqueous solution of titanium (III) chloride, and then the mixture was stirred at room temperature for 45 min. The reaction solution was added to saturated aqueous solution of sodium hydrogen carbonate and then extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. The drying agent was removed by filtration and the residues were concentrated under reduced pressure to obtain the title compound (yellow solid, 60 mg, 78%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09126931B2
Source datasetuspto-grants-2015_09
ORD IDord-a4ec8ca2e8ab46bb903abae64f62d935
Source noteuspto-grants-2015_09