Sodium Bicarbonate → 1-({5-Chloro-2-[(phenylmethyl)oxy]phenyl}methyl)-1H-pyrazol-3-amine

Participants

Reaction Conditions

Reaction Steps

1-({5-Chloro-2-[(phenylmethyl)oxy]phenyl}methyl)-3-nitro-1H-pyrazole (for a preparation see Intermediate 54)(159 mg, 0.46 mmol) was dissolved in ethanol (10 ml). Stannous chloride (hydrated) (522 mg, 2.31 mmol) was added and the reaction was stirred and heated to 85° C. overnight under nitrogen. The reaction mixture was treated with saturated aqueous sodium bicarbonate solution. The mixture was partitioned between water and ethyl acetate. The mixture was filtered to remove the solid tin residues. The ethyl acetate layer was separated, and the aqueous layer was extracted with further ethyl acetate (2×50 ml). The combined organic fractions were concentrated in vacuo to give the title compound as an off-white solid (156 mg);

Provenance & Evidence