5-Azidonicotinamide → 3-Pyridinecarboxamide, 5-amino-

HRID 1515569Notes

Reaction equation

HRID 1515569 reaction equation
[N:1]([C:4]1[CH:5]=[N:6][CH:7]=[C:8]([CH:12]=1)[C:9]([NH2:11])=[O:10])=[N+]=[N-].[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([CH:12]=1)[C:9]([NH2:11])=[O:10]

Participants

5

Reactant 2

HCID 594794565-AzidonicotinamideHCID 178418361HCID 178418361, compound

Product 1

HCID 1737473-Pyridinecarboxamide, 5-amino-Yield 36%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

97A was hydrogenated in MeOH with 10% Pd/C (20 mg) with a hydrogen balloon for 0.5 h. The Pd/C was removed by filtration. The filtrate was concentrated to give 97B (25 mg, 36% yield for two steps). 1H NMR (400 MHz, Methanol-d4) δ ppm 7.43-7.49 (m, 1H) 8.07 (d, J=2.64 Hz, 1H) 8.22 (d, J=1.76 Hz, 1H).

Workup

  1. customThe Pd/C was removed by filtration
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-4735485e3f974634a7ae9994d18f4540
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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