Methylamine → 6-Bromo-N-methylpicolinamide

HRID 1692018Notes

Reaction equation

HRID 1692018 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8](Cl)=[O:9])[CH:5]=[CH:4][CH:3]=1.[CH3:11][NH2:12]>O1CCCC1>[Br:1][C:2]1[N:7]=[C:6]([C:8]([NH:12][CH3:11])=[O:9])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 156617246-Bromopyridine-2-carbonyl chloride

Product 1

HCID 220497386-Bromo-N-methylpicolinamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-ff37692ecba245c5b9547c58be6193dc
Source dataset
uspto-grants-2012_04
Patent number
US08153813B2

Reaction notes

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