Sodium Chloride → HCID 19036607, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:14]3[N:13]([CH2:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19])[CH:12]=[CH:11][C:10]=3[CH2:9][CH2:8][C:7]=2[CH:21]=1.[OH-:22].[K+].[Cl-].[Na+].[CH2:26]([OH:29])[CH2:27]O.[OH2:30]>>[C:18]([OH:20])(=[O:30])/[CH:19]=[CH:27]/[C:26]([OH:29])=[O:22].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:14]3[N:13]([CH2:15][CH2:16][NH2:17])[CH:12]=[CH:11][C:10]=3[CH2:9][CH2:8][C:7]=2[CH:21]=1Participants
5
Procedure
0.5 g of N-[2-(4,5-dihydro-7-methoxy-1H-benz[g]indol-1-yl)ethyl]-acetamide were heated to 140° for 23 hours under argon in 21 ml of ethylene glycol/water 2:1 in the presence of 0.60 g of potassium hydroxide. The reaction mixture was left to cool and poured into 100 ml of semi-concentrated sodium chloride solution. The mixture was extracted three times with diethyl ether. The combined extracts were washed once with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated. The crude product was dissolved in 20 ml of diethyl ether and added dropwise to a solution of 245 mg of fumaric acid in 20 ml of methanol. The mixture was left to stir for one hour. and the yellowish crystals were filtered off under suction. 241 mg (38%) of 2-(4,5-dihydro-7-methoxy-1H-benz[g]indol-1-yl)-ethylamine fumarate (1:0.8) with m.p. 195° were obtained.