2-(2-氨基苯胺基)乙醇

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: According to the procedure of B. Agai, et al., Tetrahedron, 32, 839, (1976), to a cooled (0° C.), stirred suspension of 2-(2-aminoanilino)ethanol (30.4 g, 0.200 mol) in MeOH (100 mL) was added a solution of CH3NCS (14.6 g, 0.200 mol) in MeOH (60 mL) dropwise. The resulting mixture was stirred at room temperature for 4 hours and then heated under reflux for 15 minutes. CH3I (28.4 g, 0.200 mol) was added and the mixture was heated under reflux for 10 minutes, cooled to room temperature and stirred for 2 hours. Ether (200 mL) was added and the resulting precipitate was collected by filtration, taken up in nBuOH (140 mL), and heated under reflux for 10 hours. The mixture was cooled in the freezer for 3 hours and the white crystals were filtered. The material was dissolved in H2O and the solution was neutralized with 10% aqueous K 2 CO3. The white solid was collected by filtration to give 8.2 g (21%) of product m.p. >200° C. The resulting mixture was stirred at room temperature for 4 hours heated under reflux for 15 minutes the mixture was heated under reflux for 10 minutes cooled to room temperature stirred for 2 hours the resulting precipitate was collected by filtration heated under reflux for 10 hours The mixture was cooled in the freezer for 3 hours the white crystals were filtered The material was dissolved in H2O The white solid was collected by filtration

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: According to the procedure of B. Agai, et al., Tetrahedron, 32, 839, (1976), a mixture of 2-(2-nitroanilino)ethanol (43.1 g, 0.237 mol), SnCl2.2 H2O (267.0 g, 1.18 mol), and EtOH (400 mL), was heated under reflux for 4 hours. The mixture was cooled, made basic (pH8) with 2.5N NaOH, and filtered through Celite. The filtrate was concentrated to remove the EtOH and the aqueous phase was extracted with EtOAc. The combined extracts were washed with H2O and brine, dried, and concentrated. Recrystallization from EtOH gave 31.0 g (86%) of a brown solid m.p. 105°-106° C. under reflux for 4 hours The mixture was cooled filtered through Celite The filtrate was concentrated to remove the EtOH the aqueous phase was extracted with EtOAc The combined extracts were washed with H2O and brine dried concentrated Recrystallization from EtOH