Improved Process for the Preparation of 6-Chloro-5-(2-chloroethyl)oxindole

doi:10.1021/OP800105J

Paper

Improved Process for the Preparation of 6-Chloro-5-(2-chloroethyl)oxindole

Published Sep 20, 2008 · D. Nadkarni, James F. Hallissey

Organic Process Research & Development

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Abstract

The current process for ziprasidone involves preparation and isolation of the key intermediate 6-chloro-5-(2-chloroethyl)oxindole. An improved process for the synthesis of this intermediate is reported here. The new process involves use of a novel Lewis acid-mediated selective deoxygenation of the precursor ketone with tetramethyldisiloxane. The new method affords the desired compound in a one-pot process obviating the need for isolation of the potentially hazardous precursor ketone. This process was successfully scaled up to multikilo scale.

Study Snapshot

The improved process for synthesis of 6-chloro-5-(2-chloroethyl)oxindole eliminates the need for isolation of potentially hazardous precursor ketone, enabling multikilo-scale production.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Improved Process for the Preparation of 6-Chloro-5-(2-chloroethyl)oxindole

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References

Citations

Role of H and OH surface species in the reduction of the C O double bond

Metal oxides and oxide supported metals can reduce carbon-oxygen double bonds, with reactivity determined by acid-base properties and valence shell electrons structure.

Tetramethyldisiloxane: A Practical Organosilane Reducing Agent

TMDS is a safe alternative to H2, LiAlH4, and other reactive reagents for reducing functional groups and carbon-carbon bond formation in various synthetic applications.

Design of Experiments (DoE) and Process Optimization. A Review of Recent Publications

Design of experiments (DoE) is a powerful tool for optimizing processes in API development, enabling efficient scale-up and application of findings to scale-up.

Crystal structure of 1-ethyl-5-iodoindolin-2-one

1-ethyl-5-iodoindolin-2-one crystallizes in columns and interacts with neighboring molecules through hydrogen bonds and short contacts, forming a one-dimensional zigzag iodine chain along the a axis.

Hydrogenation of aromatic aldehydes to aromatic hydrocarbons over Cu-HZSM-5 catalyst

Cu-HZSM-5 catalyst effectively hydrogenates aromatic aldehydes to aromatic hydrocarbons, with its strong acidity accelerating the reaction through hydrogen spillover and C-O activation effects.