Sodium Hydroxide → (3-Morpholin-4-yl-phenyl)-hydrazine

Participants

Reaction Steps

To a cooled (−5 ° C.) solution of 3-morpholin-4-yl-phenylamine (44)(0.18 g, 1.00 mmol) in 2M HCl(aq) was added sodium nitrite (69 mg, 1.00 mmol in 1 ml water) dropwise. The red solution was stirred at −5° C. for 10 minutes before the addition of tin (II) chloride dihydrate (1.13 g, 5.0 mmol). The mixture was stirred vigorously and allowed to warm to room temperature over the period of 1 hour. 2M NaOH(aq) was added until the solution was basic (pH=8), then extracted with EtOAc (2×20 ml). The combined organic extracts were dried using MgSO4, filtered and concentrated in vacuo to give the desired product (0.15 g, 79.0%) (3-Morpholin-4-yl-phenyl)-hydrazine. m/z (LC-MS, ESP): 194.4 [M+H]+, R/T=1.00 mins.

Provenance & Evidence