5-Cyanoquinoline → 1-(Quinolin-5-yl)methanamine

HRID 1861672Notes

Reaction equation

HRID 1861672 reaction equation
[N:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]#[N:12])[C:5]=2[CH:4]=[CH:3][CH:2]=1>N.[Ni].CCO>[NH2:12][CH2:11][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[CH:3][CH:2]=[N:1]2

Participants

5

Reactant 1

HCID 47150285-Cyanoquinoline

Product 1

HCID 120186931-(Quinolin-5-yl)methanamine

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 702EthanolSolvent

Procedure

To a solution of 0.1173 g (0.76 mmol) 11 in 10 mL NH3 saturated EtOH was added a 1 mL slurry of Raney nickel (50wt. % in EtOH). After 19 h under H2 at atmospheric pressure, the reaction mixture was diluted with 20 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 (20×120 mm silica gel, linear gradient 5-7% (10% NH4OH:MeOH):CH2C2) provided 12. 1H NMR (CDCl3, 400 MHz) δ 8.937 (dd, 1H, J=1.56, 4.12 Hz, ArH); 8.475 (d, 1H, J=8.14 Hz, ArH); 8.033 (d, 1H, J=8.50 Hz, ArH); 7.681 (t, 1H, J=7.78 Hz, ArH); 7.546 (d, 1H, J=7.04 Hz, ArH); 7.450 (dd, 1H, J=4.16, 8.55 Hz, ArH); 4.347 (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 (20×120 mm silica gel, linear gradient 5-7% (10% NH4OH:MeOH):CH2C2)

Sources & evidence

ORD record
ord-3183d419d81541578f0481a80413ac15
Source dataset
uspto-grants-2003_03
Patent number
US06534510B2

Reaction notes

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