Ammonia → 3-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl) ethyl]-1H-indole-5-carbonitrile

Reaktionsgleichung

Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][N:13]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]1=[O:23].N.[CH3:25][N:26]1CCCC1=O>>[O:23]=[C:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21](=[O:22])[N:13]1[CH2:12][CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([C:25]#[N:26])[CH:3]=2)[NH:7][CH:6]=1

Komponenten

Edukt 3

HCID 222Ammonia

HCID 13387N-methyl-2-pyrrolidone

HCID 199709945-bromo-3-(2-phthalimidoethyl)-1H-indole

Produkt 1

HCID 103809773-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl) ethyl]-1H-indole-5-carbonitrile

Versuchsvorschrift

A mixture of 2-[2-(5-bromo-1H-indol-3-yl) ethyl]-1H-isoindole-1,3(2H)-dione (4.0 g), cuprous cyanide (1.1 g) and N-methyl-2-pyrrolidinone (10 ml) was heated at reflux for 1 hour. The reaction mixture was poured onto ice (30 g) and concentrated ammonia (15 ml) was added and the suspension was stirred for 0.75 hour. The solid was filtered off, washed with water and methanol and was crystallised from aqueous acetone to give the title compound (2.7 g) as a fawn solid m.p. 217°-221° C. T.L.C. Silica ether Rf 0.44.