1-Isoquinolinecarbonitrile → isoquinolin-1-ylmethanamine

HRID 1861669Notes

Reaction equation

HRID 1861669 reaction equation
[C:1]1([C:11]#[N:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1>C(O)(=O)C.[Pd]>[NH2:12][CH2:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

4

Reactant 1

HCID 3060571-Isoquinolinecarbonitrile

Product 1

HCID 1419103isoquinolin-1-ylmethanamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 0.4999 g (3.24 mmol) 1-isoquinolinecarbonitrile (1) (Aldrich) in 15 mL glacial acetic acid was added 0.0564 g Pd (10% on C). After 16 h under H2 at atmospheric pressure, the reaction mixture was filtered over celite. The celite was washed with 75 mL EtOAc, and the filtrate was concentrated in vacuo. To this was added 100 mL n-heptane, and the mixture concentrated in vacuo. The above step was repeated three times to remove acetic acid. Purification by flash chromatography (40×220 mm silica gel, linear gradient 5-10% (10% NH4OH:MeOH):CH2C12) yielded 2. 1H NMR (CDCl3, 400 MHz) δ 8.479 (d, 1H, J=5.76 Hz, ArH); 8.135 (d, 1H, J=8.42 Hz, ArH); 7.848 (d, 1H, J=8.41 Hz, ArH); 7.714-7.673 (m, 1H, ArH); 7.639-7.597 (m, 1H, ArH); 7.563 (d, 1H, J=5.67 Hz, ArH); 4.517 (s, 2H, ArCH2); MS (FAB): m/z 159.08 (M30 H).

Workup

  1. filtrationthe reaction mixture was filtered over celite
  2. washThe celite was washed with 75 mL EtOAc
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionTo this was added 100 mL n-heptane
  5. concentrationthe mixture concentrated in vacuo
  6. customto remove acetic acid
  7. customPurification by flash chromatography (40×220 mm silica gel, linear gradient 5-10% (10% NH4OH:MeOH):CH2C12)
  8. customyielded 2

Sources & evidence

ORD record
ord-c517b05af7e24fe99ea6ea515c29f136
Source dataset
uspto-grants-2003_03
Patent number
US06534510B2

Reaction notes

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