5-(Azidomethyl)isoquinoline → (Isoquinolin-5-yl)methanamine

HRID 1861675Notes

Reaction equation

HRID 1861675 reaction equation
[N:1]([CH2:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][N:9]=[CH:10]2)=[N+]=[N-]>CCOC(C)=O.[Pd]>[NH2:1][CH2:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][N:9]=[CH:10]2

Participants

4

Reactant 1

HCID 120186955-(Azidomethyl)isoquinoline

Product 1

HCID 12018696(Isoquinolin-5-yl)methanamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 0.0282 g (0.15 mmol) 17 in 1 mL EtOAc was added 0.0034 g Pd (10% on C). After 5 h under H2 at atmospheric pressure, the reaction mixture was diluted with 30 mL EtOAc and filtered over celite. The celite was washed with 200 mL EtOAc, and the filtrate was concentrated in vacuo. Purification by flash chromatography (10×160 mm silica gel, 5% (10% NH40H:MeOH):CH2Cl2) yielded 18. 1H NMR (CDCl3, 400 MHz) δ 9.272 (s, 1H, ArH); 8.583 (d, 1H, J=5.94 Hz, ArH); 7.876 (dd, 2H, J=7.18, 11.57 Hz, ArH); 7.583 (t, 1H, J=7.64 Hz, ArH); MS (Electrospray): m/z 159.0 (M+H).

Workup

  1. filtrationfiltered over celite
  2. washThe celite was washed with 200 mL EtOAc
  3. concentrationthe filtrate was concentrated in vacuo
  4. customPurification by flash chromatography (10×160 mm silica gel, 5% (10% NH40H:MeOH):CH2Cl2)

Sources & evidence

ORD record
ord-cc09254dcc88490eb62473c448fbd74e
Source dataset
uspto-grants-2003_03
Patent number
US06534510B2

Reaction notes

Loading…