Methylamine → 6-(Methylamino)pyridine-3-carbonitrile

HRID 644744Notes

Reaction equation

HRID 644744 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][CH:3]=1.[CH3:10][NH2:11]>>[CH3:10][NH:11][C:2]1[N:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 178608996-(Methylamino)pyridine-3-carbonitrile

Conditions

Temperature
80 °C

Procedure

Four batches of 6-chloro-3-pyridinecarbonitrile (0.40 g, 2.89 mmol) in methylamine (16 mL, 2M solution in THF) were each heated at 80° C. for 30 minutes in a microwave reactor. The reaction mixtures were combined and concentrated in vacuo. The residue was re-dissolved in EtOAc/water and the organic layer was separated, dried (Na2SO4) and concentrated. The crude product was purified by column chromatography; elution with EtOAc/petroleum ether gave the title compound as a white solid (1.46 g). δH (CDCl3, 400 MHz) 8.37 (1H, d), 7.59 (1H, dd), 6.39 (1H, dd), 5.19 (1H, br.s), 2.99 (3H, d). MS (ES): MH+ 134.2.

Workup

  1. customThe reaction mixtures
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was re-dissolved in EtOAc/water
  4. customthe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography
  8. washelution with EtOAc/petroleum ether

Sources & evidence

ORD record
ord-69078ad201eb4d15bc198d89f0a5dc5a
Source dataset
uspto-grants-2010_04
Patent number
US07700599B2

Reaction notes

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