Sodium hydride → HCID 19867677, compound

HRID 1199061Notes

Reaction equation

HRID 1199061 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9])(=[O:3])[CH3:2].[H-].[Na+].Cl[CH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[N:14]1[C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[N:26][C:27]([Cl:33])=[CH:28][CH:29]=2)[N:24]=1>O1CCCC1>[C:1]([NH:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][CH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[N:14]1[C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[N:26][C:27]([Cl:33])=[CH:28][CH:29]=2)[N:24]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 141824043-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinoneHCID 15732297N-(4-Hydroxybutyl)acetamide

Product 1

HCID 19867677HCID 19867677, compoundYield 6.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The procedure is as in Example 7, but starting with 4-acetylaminobutanol (6 g) in anhydrous tetrahydrofuran (250 cc), an oily suspension (50% by weight; 2.3 g) of sodium hydride and 3-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone (10 g). The product obtained is purified by chromatography on neutral alumina (40 g) contained in a column 1.5 cm in diameter, and eluting with methylene chloride and collecting 10-cc fractions. Fractions 3 to 50 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C., and the residue obtained is crystallized by stirring into 2-propanol. 3-(4-Acetylaminobutoxy)-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone (0.8 g), m.p. 120° C., is thereby obtained.

Workup

  1. customThe product obtained
  2. customis purified by chromatography on neutral alumina (40 g)
  3. washeluting with methylene chloride
  4. customcollecting 10-cc fractions
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C.
  6. customthe residue obtained
  7. customis crystallized

Sources & evidence

ORD record
ord-3bf84b02e7074750b3773f7be79aefe5
Source dataset
uspto-grants-1990_02
Patent number
US04898871

Reaction notes

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