Methylamine → 6-Bromo-N-methylpicolinamide

A solution of 6-bromopicolinoyl chloride (Example 69A, 350 mg, 1.6 mmol) in tetrahydrofuran (4 mL) was added in portions via a pipette over 2 minutes to a solution of methylamine (40 wt. % in water, 4 mL, 46.2 mmol) in tetrahydrofuran (6 mL). The mixture was stirred for 15 minutes and partitioned between water (5 mL) and CH2Cl2 (25 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (25 mL). The combined CH2Cl2 layers were dried (MgSO4), filtered and concentrated to provide the desired product, 6-bromo-N-methylpicolinamide. 1H NMR (300 MHz, CDCl3) δ ppm 3.03 and 3.04 (s and s, 3H), 7.45 and 7.60 (dd and dd, J=8.1, 1.0 Hz, 1H), 7.71 and 7.82 (t, J=7.8 Hz, 1H), 7.75-7.88 (bs, 1H), 8.11-8.18 (m, 1H); MS (DCI/NH3) m/z 215 (M+H)+.

1. custompartitioned between water (5 mL) and CH2Cl2 (25 mL)
2. customThe layers were separated
3. extractionthe aqueous layer was extracted with CH2Cl2 (25 mL)
4. dry with materialThe combined CH2Cl2 layers were dried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated

ORD record

ord-174535e4f20248589a3d9cbfedea4839

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08580968B2