Water → 4-Azido-2-(7-hydroxy-1-naphthalenyl)-1H-isoindole-1,3(2H)-dione

HRID 1413352Notes

Reaction equation

[N+:1]([C:4]1[CH:25]=[CH:24][CH:23]=[C:6]2[C:7]([N:9]([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([OH:22])[CH:20]=4)[CH:15]=[CH:14][CH:13]=3)[C:10](=[O:11])[C:5]=12)=[O:8])([O-])=O.[N-:26]=[N+:27]=[N-].[Na+].O>CS(C)=O>[N:1]([C:4]1[CH:25]=[CH:24][CH:23]=[C:6]2[C:7]([N:9]([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([OH:22])[CH:20]=4)[CH:15]=[CH:14][CH:13]=3)[C:10](=[O:11])[C:5]=12)=[O:8])=[N+:26]=[N-:27]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2.4 g (0.007 mol) of 1-(3-nitrophthalimidyl)-7-hydroxynaphthalene and 0.52 g (0.008 mol) of sodium azide in 14 ml of dimethylsulphoxide is stirred for 24 hours at 80° C. 100 ml of water are added to the solution. The crystals which have precipitated are filtered off with suction, washed with water and dried at 80° C./100 mm Hg. 1.7 g (73.6% of theory) of 1-(3-azidophthalimidyl)-7-hydroxynaphthalene are obtained; melting point 154° C. (with decomposition). IR spectrum (KBr): 1775 and 1720 cm-1 (CO--N--CO); 2130 cm-1 (N3).

Workup

customThe crystals which have precipitated
filtrationare filtered off with suction
washwashed with water
customdried at 80° C./100 mm Hg

Sources & evidence

ORD record: ord-eb0c917b3f6c45a2bebd9ce889c8d58c
Source dataset: uspto-grants-1981_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04250096

Reaction notes

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