Dimethylformamide → 2-Pyridinecarboxamide

HRID 1092819Notes

Reaction equation

HRID 1092819 reaction equation
[H-].[Na+].[NH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.C[N:10](C)[CH:11]=[O:12]>>[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:11]([NH2:10])=[O:12]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 8082PiperidineHCID 24758Sodium hydride

Product 1

HCID 150702-Pyridinecarboxamide

Procedure

Meanwhile sodium hydride (150 mg of a 60% dispersion in mineral oil) is added to a solution of N-(3,5-dichloro-1-oxido-4-pyridinio)acetamide (663 mg) in dimethylformamide (20 mL) and the mixture stirred for 2 hours. The mixture is then added to the solution of the acid chloride and stirring continued for 3 hours. Piperidine (0.26 mL) is added and stirring continued for a further 4 hours. After concentrating in vacuo the residue is dissolved in dichloromethane, the mixture filtered, the filtrate treated with decolourizing charcoal and refiltered. Evaporation in vacuo gives a brown oil which is purified by reverse phase high pressure liquid chromatography (methanol/water 4:1 v/v) to give (±)-N-(3,5-dichloro-1-oxido-4-pyridinio)-5-methoxy-4-(tricyclo[2.2.1.0.2.6]hept-2-yloxy)pyridine-2-carboxamide (60 mg) as a solid, m.p. 235-6° C. [Elemental analysis: C, 54.16; H, 4.21; N, 10.58% calculated: C, 56.04; H, 4.06; N, 9.95%].

Workup

  1. stirringstirring
  2. waitcontinued for 3 hours
  3. stirringstirring
  4. waitcontinued for a further 4 hours
  5. concentrationAfter concentrating in vacuo the residue
  6. dissolutionis dissolved in dichloromethane
  7. filtrationthe mixture filtered
  8. additionthe filtrate treated with decolourizing charcoal
  9. customEvaporation in vacuo
  10. customgives a brown oil which
  11. customis purified by reverse phase high pressure liquid chromatography (methanol/water 4:1 v/v)

Sources & evidence

ORD record
ord-64731eb9a66e4f64ba8648a12f58e66a
Source dataset
uspto-grants-2012_03
Patent number
US08129537B2

Reaction notes

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