Methylamine → 4-Chloro-N-methylpicolinamide

HRID 1640103Notes

Reaction equation

HRID 1640103 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([O:10]C)=O)[CH:3]=1.[CH3:12][NH2:13]>CO.C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:13][CH3:12])=[O:10])[CH:3]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 820890Methyl 4-Chloropicolinate

Product 1

HCID 14768144-Chloro-N-methylpicolinamideYield 84%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 4-chloropyridine-2-carboxylate (29.9 g, 174.9 mmol) in MeOH (15 mL) at 0° C. was added 2M methylamine in THF (437 mL, 874 nunol) dropwise. The reaction was allowed to stir at 0° C. for 3 h. The mixture was then concentrated and extracted with EtOAc (2×). The organic solutions were combined, washed with brine, dried over Na2SO4 and concentrated to give 4-chloro-N-methylpyridine-2-carboxamide (25 g, 84%). 1H NMR (300 MHz, d6-DMSO) δ: 8.85 (br s, 1H), 8.61 (d, 1H), 8.00 (d, 1H), 7.74 (dd, 1H), 2.81 (d, 3H).

Workup

  1. concentrationThe mixture was then concentrated
  2. extractionextracted with EtOAc (2×)
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4bbffa3a32224c1980feaccd2b37412f
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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