HCID 13355660, compound → HCID 13355752, compound
Reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([CH:10]([OH:16])[CH2:11][NH:12][CH:13]2[CH2:15][CH2:14]2)=[CH:4][C:3]=1Br.[H][H]>CO>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH:10]([OH:16])[CH2:11][NH:12][CH:13]2[CH2:15][CH2:14]2)=[CH:6][C:7]=1[C:8]#[N:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
4 gm of 1-(4'-amino-3'-bromo-5'-cyano-phenyl)-2-cyclopropylamino-ethanol was dissolved in methanol, and the solution was hydrogenated at room temperature at a hydrogen pressure of 3 to 5 atmospheres after addition of 1 gm of palladized coal (10%). After termination of hydrogen absorption, the catalyst was suction-filtered off, the filtrate was evaporated to dryness in vacuo, and the residue was distributed between dilute sodium hydroxide and chloroform. After evaporation of the chloroform phase, 1-(4'-amino-3'-cyano-phenyl)-2-cyclopropylamino-ethanol was obtained as an oil, which was purified chromatographically on silicagel (eluant: chloroform:methanol = 9:1). The dihydrochloride, obtained by addition of ethereal hydrochloric acid, was recrystallized from isopropanol. M.p. 148°-151° C. (decomp.).