Reaction #41804

Reaction equation

1

2-Fluoro-3-(4-methyl-piperazin-1-yl)-6-nitro-phenylamine

hydroxylamine HCl

pyridine

→

2

3-Fluoro-4-(4-methyl-piperazin-1-yl)-benzene-1,2-diamine

Solvents

ethanol

Conditions

Workup

1. 1
   OtherThe resulting reaction mixture
2. 2
   ConcentrationThe crude product was concentrated
3. 3
   Otherabsorbed onto silica gel
4. 4
   Otherpurified by flash chromatography (97:3 CH2Cl2/MeOH

Procedure

A 50 mL round bottom flask was charged with 1 (680 mg, 2.5 mmol), hydroxylamine HCl (191 mg, 2.75 mmol), pyridine (0.25 mL, 3.0 mmol) and ethanol (10 mL). The resulting reaction mixture was stirred at rt overnight. The crude product was concentrated, absorbed onto silica gel, and purified by flash chromatography (97:3 CH2Cl2/MeOH to give 2 as an orange solid. LCMS m/z 289.2 (MH+), tR=2.06 min.

Source