2-(cyclopropylmethoxy)aniline

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-(cyclopropylmethoxy)aniline (1.03 g, 6.31 mmol) in pyridine (20 ml) was cooled to 0° C., and methanesulfonyl chloride (0.541 ml, 6.94 mmol) was added. The mixture was warmed to RT and stirred for 2 hours. The solvent was removed, and the crude was portioned between EtOAc and HCl 1N. The organic phase was washed with brine and dried over Na2SO4. The solvent was removed and the crude was purified by filtration on silica gel cartridge (petroleum ether:EtOAc=80:20) affording N-(2-(cyclopropylmethoxy)phenyl)methanesulfonamide (1.456 g, 6.03 mmol, 96% yield, MS/ESI+ 263.9 [MNa]+). The solvent was removed The organic phase was washed with brine dried over Na2SO4 The solvent was removed the crude was purified by filtration on silica gel cartridge (petroleum ether:EtOAc=80:20)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1-(cyclopropylmethoxy)-2-nitrobenzene (1.352 g, 7.00 mmol) and 10% Pd/C (0.140 g, 0.132 mmol) in MeOH (30 ml) was hydrogenated at 20 psi for 1 hour. The catalyst was filtered off, and the solvent was removed affording 2-(cyclopropylmethoxy)aniline (1.03 g, 6.31 mmol, 90% yield, MS/ESI+ 164.0 [MH]+) that was used in the next step without further purification. The catalyst was filtered off the solvent was removed