8-(Azidomethyl)quinoline → (Quinolin-8-yl)methanamine

HRID 1861677Notes

Reaction equation

HRID 1861677 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][CH:11]=[CH:10]2)=[N+]=[N-]>CCOC(C)=O.[Pd]>[NH2:1][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][CH:11]=[CH:10]2

Participants

4

Reactant 1

HCID 120186978-(Azidomethyl)quinoline

Product 1

HCID 15079229(Quinolin-8-yl)methanamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 0.8432 g (4.58 mmol) 21 in 20 mL EtOAc was added 0.0880 g Pd (10% on C). After 19 h under H2 at atmospheric pressure, the reaction mixture was diluted with 25 mL EtOAc and filtered over celite. The celite was washed with 150 mL EtOAc, and the combined organics were dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (40×140 mm silica gel, linear gradient 5-15% (10% NH4OH:MeOH):CH2Cl2) gave 22. 1H NMR (CDCl3, 400 MHz) δ 8.936 (dd, 1H, J=1.78, 4.16 Hz, ArH); 8.165 (dd, 1H, J=1.69, 8.28 Hz, ArH); 7.730 (dd, 1H, J=1.10, 8.14 Hz, ArH); 7.652 (dd, 1H, J=0.64, 7.03 Hz, ArH); 7.497 (t, 1H, J=7.59 Hz, ArH); 7.421 (dd, 1H, J=4.22, 8.23 Hz, ArH); 4.433 (s, 2H, ArCH2); MS (FAB): m/z 159.09 (M+H).

Workup

  1. filtrationfiltered over celite
  2. washThe celite was washed with 150 mL EtOAc
  3. dry with materialthe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (40×140 mm silica gel, linear gradient 5-15% (10% NH4OH:MeOH):CH2Cl2)

Sources & evidence

ORD record
ord-68f54945a4a340e3b42e85a6946c7a71
Source dataset
uspto-grants-2003_03
Patent number
US06534510B2

Reaction notes

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