Water → HCID 22163828, compound

HRID 1087779Notes

Reaction equation

[H-].[Na+].[OH:3][CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=O)[N:5]1[C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[N:17][C:18]([O:24][CH3:25])=[CH:19][CH:20]=2)[N:15]=1.[CH3:26][C:27](=[O:32])[CH2:28][CH2:29][CH2:30][CH3:31].O>CN(C)C=O>[CH3:25][O:24][C:18]1[N:17]=[C:16]2[C:21]([CH:22]=[CH:23][C:14]([N:5]3[CH:6]([CH2:26][C:27](=[O:32])[CH2:28][CH2:29][CH2:30][CH3:31])[C:7]4[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:4]3=[O:3])=[N:15]2)=[CH:20][CH:19]=1

Participants

Conditions

Temperature: -5 °C

Procedure

An oily suspension (50% by weight; 3.1 g) of sodium hydride is added in small portions at a temperature in the region of -5° C. to a solution, maintained under a nitrogen atmosphere, of 3-hydroxy-2-(7-methoxy-1,8-naphthyridin-2-yl)-1-isoindolinone (10 g) in anhydrous dimethylformamide (195 cc), and the suspension obtained is stirred for 30 minutes at a temperature in the region of -5° C. A solution of 2-hexanone (6.5 g) in anhydrous dimethylformamide (5 cc) is then added and stirring is continued for 8 hours at a temperature in the region of 0° C. and then for 16 hours at a temperature in the region of 20° C. The reaction mixture is then poured into water (1.5 litres). The solid obtained is separated by filtration, washed with water and dried in the air. After recrystallization in ethanol, 2-(7-methoxy-1,8-naphthyridin-2-yl)-3-(2-oxohexyl)-1-isoindolinone (3.6 g), m.p. 161° C., is obtained.

Workup

customthe suspension obtained
stirringstirring
waitis continued for 8 hours at a temperature in the region of 0° C.
waitfor 16 hours at a temperature in the region of 20° C
customThe solid obtained
customis separated by filtration
washwashed with water
customdried in the air
customAfter recrystallization in ethanol

Sources & evidence

ORD record: ord-14c5a828a593499890f89f1da58b33ff
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04960779

Reaction notes

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