Phenyl chloroformate → 2-(7-Chloro-1,8-naphthyridin-2-yl)-3-phenoxycarbonyloxy-1-isoindolinone

HRID 27073

Reaction equation

Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[Cl:11][C:12]1[N:21]=[C:20]2[C:15]([CH:16]=[CH:17][C:18]([N:22]3[CH:30]([OH:31])[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:23]3=[O:32])=[N:19]2)=[CH:14][CH:13]=1>N1C=CC=CC=1>[Cl:11][C:12]1[N:21]=[C:20]2[C:15]([CH:16]=[CH:17][C:18]([N:22]3[CH:30]([O:31][C:2]([O:4][C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)=[O:3])[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:23]3=[O:32])=[N:19]2)=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 20 °C

Procedure

Phenyl chloroformate (126 g.) is added to a suspension of 2-(7-chloro-1,8-naphthyridin-2-yl)-3-hydroxy-isoindolin-1-one (86.5 g.) in pyridine (980 cc.), whilst keeping the temperature at about 25° C. The reaction mixture is stirred for 3 hours at a temperature of about 20° C. and then poured into ice-water (9,000 cc.). The product which crystallises is filtered off, washed with water (6×500 cc.) and then with acetonitrile (3×200 cc.). After drying, 2-(7-chloro-1,8-naphthyridin-2-yl)-3-phenoxycarbonyloxy-isoindolin-1-one (96.7 g.), which melts at 235° C. with decomposition, is obtained.

Workup

customat about 25° C
customThe product which crystallises
filtrationis filtered off
washwashed with water (6×500 cc.)
customAfter drying

Sources & evidence

ORD record: ord-6572f0c54f304f6b8594fe20750711f6
Source dataset: uspto-grants-1980_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04220646

Linked notes

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