N-[2-(9-anthryloxy)ethyl]phthalimide → Ammonium Hydroxide

Reaction equation

[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[O:15][CH2:16][CH2:17][N:18]2C(=O)C4=CC=CC=C4C2=O)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1>C(O)C.C(OCC)(=O)C>[OH-:15].[NH4+:18].[CH:11]1[C:12]2[C:7](=[CH:6][C:5]3[C:14]([C:13]=2[O:15][CH2:16][CH2:17][NH2:18])=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:8]=[CH:9][CH:10]=1

Participants

Procedure

N-[2-(9-anthryloxy)ethyl]phthalimide (6.5 g) was refluxed for 3 hours in ethanol containing 85% hydrazine hydrate (3.0 ml). The solution was cooled and diluted with ethyl acetate. The resultant solution was washed with dilute aqueous potassium hydroxide, dried and evaporated. The crude product was chromatographed on 300 g silica gel, eluting with a solution of methylene chloride:methanol:ammonium hydroxide, 95:4:1, yielding 1-(9-anthryloxy)-2-aminoethane, which was converted to the maleate, mp 190°-195° C., according to the method of Example 3.