Reaction #1135837

Reaction equation

KOH

methyl 7-(6-phenyl-1H-benzo[d]imidazol-2-yl)heptanoate

hydroxylamine

→

N-hydroxy-7-(6-phenyl-1H-benzo[d]imidazol-2-yl)heptanamide

Yield 53.3%

Solvents

THF

Conditions

Workup

1. 1
   Concentrationbriefly concentrated
2. 2
   workup.ADDITIONby adding 1 N HCl solution until pH was 7
3. 3
   FiltrationThe white precipitate was collected by filtration
4. 4
   Otherpurified by biotage column chromatography

Procedure

To a solution of methyl 7-(6-phenyl-1H-benzo[d]imidazol-2-yl)heptanoate (50 mg, 0.15 mmol) in THF at 0° C. was added 50% hydroxylamine solution (0.10 mL, 1.5 mmol). To this was added KOH (0.45 mL, 1M in MeOH, 0.45 mmol) dropwise. The reaction was stirred at 0° C. for 2 hr, briefly concentrated and neutralized by adding 1 N HCl solution until pH was 7. The white precipitate was collected by filtration and purified by biotage column chromatography to give N-hydroxy-7-(6-phenyl-1H-benzo[d]imidazol-2-yl)heptanamide 18 (27 mg). MS (M+1=338)

Source