Water → HCID 57316045, compound

HRID 1029502Notes

Reaction equation

N1C=CC=CC=1.[C:7](Cl)(=[O:10])[CH2:8][CH3:9].[Cl:12][C:13]1[N:22]=[C:21]2[C:16]([CH:17]=[CH:18][C:19]([N:23]3[CH:31]([OH:32])[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:24]3=[O:33])=[N:20]2)=[CH:15][CH:14]=1.O>C(Cl)Cl>[C:7]([O:33][CH:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:31](=[O:32])[N:23]1[C:19]1[CH:18]=[CH:17][C:16]2[C:21](=[N:22][C:13]([Cl:12])=[CH:14][CH:15]=2)[N:20]=1)(=[O:10])[CH2:8][CH3:9]

Participants

Conditions

Temperature: 25 °C

Procedure

Pyridine (24 cc) followed, in the course of 30 minutes, by propionyl chloride (5.5 g) are added successively to a solution of 2-(7-Chloro-1,8-naphthyridin-2-yl)-3-hydroxy-1-isoindolinone (3.2 g) in methylene chloride (160 cc), while the temperature is maintained in the region of 25° C. The mixture is stirred for 3 hours at this temperature and then treated with water (100 cc). The organic phase is separated after settling has occurred, washed with water, dried and concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is crystallized in isopropyl ether and then recrystallized in a mixture of isopropyl ether and ethyl acetate (25:75 by volume). 2-(7-Chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl propionate (1 g), m.p. 160° C., is thereby obtained.

Workup

customThe organic phase is separated after settling
washwashed with water
customdried
concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
customThe residue obtained
customis crystallized in isopropyl ether
customrecrystallized in a mixture of isopropyl ether and ethyl acetate (25:75 by volume)

Sources & evidence

ORD record: ord-28b18fd774ee47eebf7842fceb381d66
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05102890

Reaction notes

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