Methylamine → 4-Chloro-N-methylpicolinamide

HRID 658466Notes

Reaction equation

HRID 658466 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]([O:11]C)=O)[CH:4]=1.[CH3:13][NH2:14]>CO.C1COCC1>[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]([NH:14][CH3:13])=[O:11])[CH:4]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 16655470Methyl 4-chloropyridine-2-carboxylate--hydrogen chloride (1/1)

Product 1

HCID 14768144-Chloro-N-methylpicolinamideYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of methyl 4-chloropyridine-2-carboxylate HCl salt (89.0 g, 428 mmol) in MeOH (75 mL) at 0° C. was treated with a 2.0 M methylamine solution in THF (1 L). The resulting mixture was stored at 3° C. for 5 h, then concentrated under reduced pressure. The resulting solids were suspended in EtOAc (1L) and filtered. The filtrate was washed with a saturated NaCl solution (500 mL), dried over Na2SO4, and concentrated under reduced pressure to afford 4-chloro-N-methyl-2-pyridinecarboxamide as pale-yellow crystals (71.2 g, 97%). 1H-NMR (DMSO-d6) δ 2.81 (s, 3H), 7.74 (dd, J=5.1, 2.2 Hz, 1H), 8.00 (d, J=2.2 Hz, 1H), 8.61 (d, J=5.1 Hz, 1H), 8.85 (br d, 1H); CI-MS m/z 171 (MH+); m.p. 41-43° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. filtrationfiltered
  3. washThe filtrate was washed with a saturated NaCl solution (500 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-84584f17c1874068a8e8c5c5e0e3651d
Source dataset
uspto-grants-2011_12
Patent number
US08076488B2

Reaction notes

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