3-(Tetrazol-1-yl)cyanopyridine → 3-(Tetrazol-1-yl)-2-aminomethylpyridine

HRID 857726Notes

Reaction equation

HRID 857726 reaction equation
[N:1]1([C:6]2[C:7]([C:12]#[N:13])=[N:8][CH:9]=[CH:10][CH:11]=2)[CH:5]=[N:4][N:3]=[N:2]1>[Pd].C(O)C>[N:1]1([C:6]2[C:7]([CH2:12][NH2:13])=[N:8][CH:9]=[CH:10][CH:11]=2)[CH:5]=[N:4][N:3]=[N:2]1

Participants

4

Reactant 1

HCID 218662973-(Tetrazol-1-yl)cyanopyridine

Product 1

HCID 112290913-(Tetrazol-1-yl)-2-aminomethylpyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-(tetrazol-1-yl)cyanopyridine (250 mg, 1.45 mmol) and 45% by weight of palladium on carbon, 10% catalyst (110 mg) in ethanol (75 ml) was placed on a PARR Hydrogenation Apparatus under a hydrogen atmosphere at 55 psi. overnight. The mixture was filtered through celite and concentrated to give 3-(tetrazol-1-yl)-2-aminomethylpyridine; 1H NMR (CD3OD) δ 9.60 (s, 1H), 8.83–8.81 (m, 1H), 7.99–7.97 (m, 1H), 7.59–7.56 (m, 1H), 3.77 (s, 2H).

Workup

  1. customovernight
  2. filtrationThe mixture was filtered through celite and
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-22c06dac5aba444ebee7847223f7c823
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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