2-Amino-6-methylpyridine → HCID 18457531, compound

Participants

Reaction Conditions

Reaction Steps

2-Amino-6-picoline (39.8 kg, 99.6 wgt % purity, 367 mol, 1.00 eq) was charged into acetic acid (65.0 kg) while the temperature rose to 60° C. Additional acetic acid (17 kg) was charged to wash in the last of the picoline and the mixture was heated to 35° C. until dissolution occurred. After cooling to 18° C., bromine (56.2 kg, 352 mol, 0.96 eq) was charged at 18±3° C. over 2 hours. More acetic acid (2.0 kg) was charged to wash in the last of the bromine. The mixture was held at this temperature range for 1 hour and then cooled to 11-15° C. It was held in this range for 0.5 hours. The solids were recovered by filtration on polypropylene and washed with isopropanol (63.0 kg) to produce 69.6 kg of moist 5-bromo-2-amino-6-picoline hydrobromide (76 wgt % of product as hydrobromide). This corresponds to a 54% yield. Part of this product was dried for the purposes of recording the 13C NMR spectrum: 13C NMR (400 MHz, DMSO-d6) δ 154.1, 146.9, 112.4, 105.2, 20.1.

Provenance & Evidence