Sulfate Ion → N-[[3-[3-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)propyl]-1H-indol-5-yl]methyl]formamide

HRID 652451Notes

Reaction equation

HRID 652451 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][CH2:14][N:15]1[C:23](=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]1=[O:25].S([O-])([O-])(=O)=O.[C:31](OC=O)(=[O:33])C>N1C=CC=CC=1>[O:24]=[C:23]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16](=[O:25])[N:15]1[CH2:14][CH2:13][CH2:12][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([CH2:2][NH:1][CH:31]=[O:33])[CH:4]=2)[NH:8][CH:7]=1

Participants

5

Reactant 3

HCID 1117Sulfate IonHCID 75269Acetic-formic anhydrideHCID 128031172-[3-[5-(aminomethyl)-1H-indol-3-yl]propyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 12803120N-[[3-[3-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)propyl]-1H-indol-5-yl]methyl]formamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Following the method described in Example 12 (i), a solution of 2-[3-[5-(aminomethyl)-1H-indol-3-yl]propyl]-1H-isoindole-1,3(2H)-dione, sulphate (0.75 g) was reacted with formic acetic anhydride (15 ml) in pyridine (27.5 ml) to give the title compound as a yellow solid (0.49 g) m.p. 150°-152° after crystallisation from ethyl acetate.

Sources & evidence

ORD record
ord-564fe3b923c44e80b63c19cca28c8544
Source dataset
uspto-grants-1987_06
Patent number
US04672067

Reaction notes

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