2-Aminopyridine → 6-amino-3-Pyridinepropanol

HRID 1355501Notes

Reaction equation

HRID 1355501 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][OH:11])=[CH:4][CH:3]=1.NC1C=CC=CN=1>CCO.[OH-].[OH-].[Pd+2]>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 104392-AminopyridineHCID 185068563-(6-Aminopyridin-3-yl)prop-2-yn-1-ol

Product 1

HCID 185068066-amino-3-Pyridinepropanol

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

3-(6-Amino-pyridin-3-yl)-prop-2-yn-1-ol (7-2), 2.73 g (18.4 mmol) and Pd(OH)2 (0.27 g) were stirred in 30 mL EtOH (aminopyridine does not completely dissolve). Reaction was put under one atmosphere of H2 for 24 h. The reaction was filtered through a plug of celite, washed with EtOH, and concnetrated to afford the titled compound as an orange oil. 1H NMR (CDCl3) δ 7.90 (d, 1H, J=2.3 Hz), 7.31 (dd, 1H, J=2.4, 8.6 Hz), 6.43 (d, 1H, J=8.7 Hz), 4.38 (bs, 2H), 3.63 (t, 2H, J=7.5 Hz), 2.58 (t, 2H, J=7.2 Hz), 1.97 (bs, 1H), 1.82 (m, 2H).

Workup

  1. dissolutiondoes not completely dissolve)
  2. customReaction
  3. filtrationThe reaction was filtered through a plug of celite
  4. washwashed with EtOH

Sources & evidence

ORD record
ord-fb35f63d604048f59a6f86e25bd95bff
Source dataset
uspto-grants-2003_07
Patent number
US06586424B2

Reaction notes

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