Methyl Isocyanate → HCID 18963976, compound

Participants

Reaction Steps

2-(3-Phenylpropyl)-6-[2-(N-hydroxyamino)-ethoxy]-1-oxo-1,2,3,4-tetrahydroisoquinoline (498 mg, 1.5 mmol) is dissolved in dioxane (15 mL) and methyl isocyanate (0.22 mL, 3.7 mmol) is added. After 12 hours, the reaction mixture is diluted with EtOAc (150 mL) and the organic phase washed with 2N HCl (2×200 mL), H2O (4×200 mL), saturated NaHCO3 solution (2×200 mL), saturated NaCl solution (2×200 mL), dried over MgSO4 and concentrated in vacuo. The resulting material is triturated with hexanes and recrystallized from CH2Cl2 /hexanes to give 2-(3-phenylpropyl)-6-{2-[N-(methylaminocarbonyl)-N-hydroxyamino]-ethoxy}-1-oxo-1,2,3,4-tetrahydroisoquinoline, m.p. 138°-139°.

Provenance & Evidence