Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Propionyl chloride | HCID 62324 | — |
| Reactant | 2-(7-Chloro-1,8-naphthyridin-2-yl)-3-hydroxyisoindolin-1-one | HCID 19900408 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 57316045 | HCID 57316045 | 26.5% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05102890 |
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| Source dataset | uspto-grants-1992_04 |
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| ORD ID | ord-28b18fd774ee47eebf7842fceb381d66 |
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| Source note | uspto-grants-1992_04 |
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