Acetic Acid → 4-(Benzyloxy)pyridin-3-amine

To a mixture containing 4-(benzyloxy)-3-nitropyridine (7.2 g, 31.3 mmol) and zinc powder (6.1 g, 91.0 mmol) was added acetic acid (7.2 mL, 7.5 mmol). The mixture was stirred for 6 h at room temperature, filtered and concentrated. The resultant residue was dissolved in ethyl acetate (300 mL), washed with aqueous, saturated ammonium chloride (3×100 mL), washed with brine (100 mL), dried over MgSO4, filtered and concentrated to afford 4-(benzyloxy)pyridin-3-amine as an orange oil which was used without further purification. 1H NMR (500 MHz, DMSO-D6) δ ppm 7.91 (s, 1H), 7.72 (d, J=5.49 Hz, 1H), 7.50 (d, J=7.63 Hz, 2H), 7.41 (t, J=7.32 Hz, 2H), 7.34 (s, 1H), 7.03 (d, J=5.49 Hz, 1H), 5.24 (s, 2H), 5.13 (s, 2H). LCMS: retention time: 1.372 min. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Phenomenex-Luna, 10 micron, C18, 4.6×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 4 mL/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 4 min, a hold time of 1 min, and an analysis time of 5 min where solvent A was 5% CH3CN/95% H2O/10 mM ammonium acetate and solvent B was 5% H2O/95% CH3CN/10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode. m/z 201 (MH+).

1. filtrationfiltered
2. concentrationconcentrated
3. dissolutionThe resultant residue was dissolved in ethyl acetate (300 mL)
4. washwashed with aqueous, saturated ammonium chloride (3×100 mL)
5. washwashed with brine (100 mL)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-019c6e4b807246a9b014bba1f77ee59e

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08536338B2