Isoquinoline-8-carbonitrile → 8-Isoquinolinemethanamine

HRID 1861679Notes

Reaction equation

HRID 1861679 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]#[N:12])[CH:4]=[CH:3][N:2]=1>N.[Ni].CCO>[NH2:12][CH2:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:1]=[N:2][CH:3]=[CH:4]2

Participants

5

Reactant 1

HCID 12018698Isoquinoline-8-carbonitrile

Product 1

HCID 120186998-Isoquinolinemethanamine

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 702EthanolSolvent

Procedure

To a solution of 0.1787 g (1.16 mmol) 25 in 10 mL NH3 saturated EtOH was added a 1 mL slurry of Raney nickel (50 wt. % in EtOH). After 22 h under H2 at atmospheric pressure, the reaction mixture was diluted with 25 mL EtOH and filtered over celite. The celite was washed with 200 mL EtOH, and the filtrate was concentrated in vacuo. Purification by flash chromatography (15×140 mm silica gel, linear gradient 5-8% (10% NH4HO:MeOH):CH2Cl2) afforded 26. 1H NMR (CDCl3, 400 MHz) δ 9.565 (s, 1H, ArH); 8.565 (d, 1H, J=5.66 Hz; ArH); 7.734 (d, 1H, J=8.13 Hz, ArH); 7.679-7.662 (m, 1H, ArH); 7.644 (d, 1H, J=8.14 Hz, ArH); 7.599 (d, 1H, J6.95 Hz, ArH); 4.460 (s, 2H, ArCH2); MS (Electrospray): m/z 159.0 (M+H).

Workup

  1. filtrationfiltered over celite
  2. washThe celite was washed with 200 mL EtOH
  3. concentrationthe filtrate was concentrated in vacuo
  4. customPurification by flash chromatography (15×140 mm silica gel, linear gradient 5-8% (10% NH4HO:MeOH):CH2Cl2)

Sources & evidence

ORD record
ord-c6c06bb0b3994c70a6c0153ef9fc0d9f
Source dataset
uspto-grants-2003_03
Patent number
US06534510B2

Reaction notes

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