Methylamine → 4-Chloro-N-methylpicolinamide

HRID 1711630Notes

Reaction equation

HRID 1711630 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.CCOC(C)=O>[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

6

Reactant 2

HCID 6329MethylamineHCID 110951464-chloropyridine-2-carbonyl Chloride

Product 1

HCID 14768144-Chloro-N-methylpicolinamideYield 60%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
3 °C

Procedure

To a solution of 4-chloro-pyridine-2-carbonyl chloride (27.6 g, 0.16 mol) in anhydrous THF (100 mL) at 0° C. was added dropwise a solution of MeNH2 in EtOH. The resulting mixture was stirred at 3° C. for 4 h. The reaction mixture was concentrated under reduced pressure to yield a solid, which was suspended in EtOAc and filtered. The filtrate was washed with brine (2×100 mL), dried and concentrated to yield 4-chloro-N-methylpicolinamide (16.4 g, 60% yield) 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. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto yield a solid, which
  3. filtrationfiltered
  4. washThe filtrate was washed with brine (2×100 mL)
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-81ff4f0af622407faeab6c1cc6c9f46e
Source dataset
uspto-grants-2010_09
Patent number
US07790756B2

Reaction notes

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