[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][CH2:9][CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[CH:6][CH:5]=1)([O-])=O.[OH-].[Na+].C(Cl)(Cl)Cl>Cl.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[CH:16][CH:17]=1Iron powder (6.0 g) was added in portions to a warm solution of 1-[2-(4-nitrophenoxy)ethyl]imidazole (3.7 g) in 5N hydrochloric acid (60 ml). After 20 minutes the solution was cooled, made basic with dilute sodium hydroxide solution and the mixture was shaken with chloroform and filtered. The chloroform layer of the filtrate was separated, dried (Na2SO4) and evaporated to give a solid which was crystallised from ethyl acetate/petrol to give 1-[2-(4-aminophenoxy)ethyl]imidazole (2.25 g) m.p. 91°-92° C. Found: C, 64.35; H, 6.40; N, 20.61. C11H13N3O requires: C, 65.01; H, 6.45; N, 20.68%.
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