Methylamine → 4-Chloro-N-methylpicolinamide

HRID 718135Notes

Reaction equation

HRID 718135 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8](Cl)=[O:9])[CH:3]=1.[CH3:11][NH2:12]>C1COCC1.CCO>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:12][CH3:11])=[O:9])[CH:3]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 110951464-chloropyridine-2-carbonyl Chloride

Product 1

HCID 14768144-Chloro-N-methylpicolinamideYield 60%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
3 °C

Procedure

A 0° C. solution of 4-chloro-pyridine-2-carbonyl chloride (27.6 g, 0.16 mol) in THF (100 mL) at was treated drop-wise with a solution of MeNH2 in EtOH, stirred at 3° C. for 4 h, then concentrated to dryness. The material was suspended in EtOAc, the solids removed via filtration and the filtrate was washed with brine (2×), dried and concentrated to yield 4-chloro-N-methylpicolinamide (16.4 g, 60%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 8.78 (br s, 1H), 8.55 (d, J=5.2 Hz, 1H), 7.97 (d, J=2.0 Hz, 1H), 7.66 (m, 1H), 2.82 (d, J=4.8 Hz, 3H); MS (ESI) m/z: 171.0 (M+H+).

Workup

  1. concentrationconcentrated to dryness
  2. customthe solids removed via filtration
  3. washthe filtrate was washed with brine (2×)
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c7792fb7b76b4daba10f23d1dd98f8f3
Source dataset
uspto-grants-2015_11
Patent number
US09193719B2

Reaction notes

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