6-Chloropicolinic acid → 6-Chloropyridine-2-carboxamide

6-Chloropyridine-2-carboxylic acid (1.20 g, 7.62 mmol) and ammonium chloride (0.81 g, 15.2 mmol) were dissolved in DMF (20 mL) and DIPEA (5.31 mL, 30.5 mmol), HONB (2.05 g, 11.4 mmol) and HBTU (4.33 g, 11.4 mmol) were added. The reaction mixture was stirred for 1 h and the solvents were removed in vacuo. The residue was partitioned between DCM (50 mL) and 1 M aq HCl (50 mL) and the aq fraction was extracted with DCM (2×25 mL). The combined organic fractions were washed with sat aq NaHCO3 (50 mL), brine (50 mL), dried (MgSO4) and concentrated in vacuo. The residue was recrystallised from MeOH/water to give the title compound (1.12 g, 94%) as a white solid. LCMS (ES+): 157.4 [MH]+.

1. customthe solvents were removed in vacuo
2. customThe residue was partitioned between DCM (50 mL) and 1 M aq HCl (50 mL)
3. extractionthe aq fraction was extracted with DCM (2×25 mL)
4. washThe combined organic fractions were washed with sat aq NaHCO3 (50 mL), brine (50 mL)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated in vacuo
7. customThe residue was recrystallised from MeOH/water

ORD record

ord-de1267a114954a9186122d9cc1d5e0e2

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09353086B2