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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 66345Generated: October 30, 2026

Pyridine → 5-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-3-n-butylaminocarbonyloxy-isoindolin-1-one

https://huagongshe.com/reaction/66345

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPyridineHCID 1049—
ReactantButyl isocyanateHCID 8110—
Reactant2-(7-Chloro-1,8-naphthyridin-2-yl)-5-chloro-3-hydroxy-isoindolin-1-oneHCID 19842242—
SolventAcetonitrileHCID 6342—
SolventTriethylamineHCID 8471—
Product5-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-3-n-butylaminocarbonyloxy-isoindolin-1-oneHCID 86735647—

Reaction Steps

n-Butyl isocyanate (11.2 cc.) is added over the course of 15 minutes to a suspension of 5-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-3-hydroxy-isoindolin-1-one (3.5 g.) in acetonitrile (350 cc.) and triethylamine (0.2 cc.) heated at the reflux temperature. Pyridine (10 cc.) and triethylamine (5 cc.) are added and refluxing is continued for a further 40 minutes. After filtering hot and then cooling, the precipitate formed is filtered off and recrystallised from acetonitrile (250 cc.) to give 5-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-3-n-butylaminocarbonyloxy-isoindolin-1-one (3.3 g.) melting at 228°-230° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04131674
Source datasetuspto-grants-1978_12
ORD IDord-2368399e39304d308304ff048f1fcfef
Source noteuspto-grants-1978_12