hydrogen; palladium on activated charcoal in methanol

1: 1-ethyl-3<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / Ambient temperature 2: H2 / 10 percent Pd/C / methanol View Scheme

1: 97.6 percent / H2 / 10percent Pd/C / toluene / 14 h / 60 - 70 °C / 3102.9 Torr 2: 55.9 percent / 192 h / Ambient temperature 3: 64 percent / diethyl ether / 24 h / Ambient temperature 4: 98 percent / 1 N HCl / CHCl3 5: 1.) CDI, 2.) Et3N / 1.) THF, RT, 2 h, 2.) THF, RT 6: KOH, HONH2*HCl / methanol / Ambient temperature View Scheme

potassium hydroxide; hydroxylamine hydrochloride in methanol Ambient temperature;

1: 100 percent / 4 N HCl / dioxane; methanol / 4 h / Ambient temperature 2: 1.) CDI, 2.) Et3N / 1.) THF, RT, 2 h, 2.) THF, RT 3: KOH, HONH2*HCl / methanol / Ambient temperature View Scheme

1: 1.) CDI / 1.) THF, RT, 2 h, 2.) THF, RT, 24 h 2: 100 percent / 4 N HCl / dioxane; methanol / 4 h / Ambient temperature 3: 1.) CDI, 2.) Et3N / 1.) THF, RT, 2 h, 2.) THF, RT 4: KOH, HONH2*HCl / methanol / Ambient temperature View Scheme

1: 64 percent / diethyl ether / 24 h / Ambient temperature 2: 98 percent / 1 N HCl / CHCl3 3: 1.) CDI, 2.) Et3N / 1.) THF, RT, 2 h, 2.) THF, RT 4: KOH, HONH2*HCl / methanol / Ambient temperature View Scheme

1: 55.9 percent / 192 h / Ambient temperature 2: 64 percent / diethyl ether / 24 h / Ambient temperature 3: 98 percent / 1 N HCl / CHCl3 4: 1.) CDI, 2.) Et3N / 1.) THF, RT, 2 h, 2.) THF, RT 5: KOH, HONH2*HCl / methanol / Ambient temperature View Scheme

1: 1.) CDI, 2.) Et3N / 1.) THF, RT, 2 h, 2.) THF, RT 2: KOH, HONH2*HCl / methanol / Ambient temperature View Scheme

1: 98 percent / 1 N HCl / CHCl3 2: 1.) CDI, 2.) Et3N / 1.) THF, RT, 2 h, 2.) THF, RT 3: KOH, HONH2*HCl / methanol / Ambient temperature View Scheme