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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1937318Generated: November 4, 2026

Methanol → 7-Chloro-5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetonitrile

https://huagongshe.com/reaction/1937318

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
ReactantTosylmethyl isocyanideHCID 161915—
Reactant7-Chloro-5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-carboxaldehydeHCID 15461902—
ReactantPotassium tert-butoxideHCID 23665647—
Solvent1,2-DimethoxyethaneHCID 8071—
Product7-Chloro-5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetonitrileHCID 15461903—

Reaction Conditions

Temperature-60 °C

Reaction Steps

1.27 g (10.96 mmol) of potassium 1,1-dimethylethoxide are added, in small portions, to a solution of 2.14 g (10.96 mmol) of 1-[(isocyanomethyl)-sulphonyl]-4-methylbenzene in 50 ml of 1,2-dimethoxyethane, the reaction mixture is stirred for 30 min at −60° C., 2.88 g (8.53 mmol) of 7-chloro-5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-carboxaldehyde are added and the reaction mixture is stirred for 3 h 30 min at −60° C. 9 ml of methanol are added and the reaction mixture is again stirred for 30 min at room temperature and for 1 h under reflux.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06395729B1
Source datasetuspto-grants-2002_05
ORD IDord-e1080a0cdbb8465799927ce0fef51c5f
Source noteuspto-grants-2002_05