Butyryl chloride → HCID 57243056, compound

HRID 1029503Notes

Reaction equation

HRID 1029503 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[CH:20]([OH:21])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:22])=[N:9]2)=[CH:4][CH:3]=1.[C:23](Cl)(=[O:27])[CH2:24][CH2:25][CH3:26]>C(Cl)Cl.N1C=CC=CC=1>[C:23]([O:22][CH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20](=[O:21])[N:12]1[C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[N:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=1)(=[O:27])[CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 2

HCID 8855Butyryl chlorideHCID 199004082-(7-Chloro-1,8-naphthyridin-2-yl)-3-hydroxyisoindolin-1-one

Product 1

HCID 57243056HCID 57243056, compoundYield 43.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

The procedure is as in Example 30, but starting with 2-(7-chloro-1,8-naphthyridin-2-yl)-3-hydroxy-1-isoindolinone (6.4 g) in methylene chloride (320 cc), pyridine (48 cc) and butyryl chloride (12.8 g). After one recrystallization in isopropyl ether followed by two recrystallizations in acetonitrile, 2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl butyrate (3.4 g), m.p. 140° C., is obtained.

Workup

  1. customAfter one recrystallization in isopropyl ether
  2. customfollowed by two recrystallizations in acetonitrile

Sources & evidence

ORD record
ord-419274cd2fb04fb8af1eaf5e8a43f6d1
Source dataset
uspto-grants-1992_04
Patent number
US05102890

Reaction notes

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