6-(2-Azidopropan-2-yl)quinoline → 2-(Quinolin-6-yl)propan-2-amine

HRID 1404769Notes

Reaction equation

HRID 1404769 reaction equation
[N:1]([C:4]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][CH:11]=[CH:10]2)([CH3:6])[CH3:5])=[N+]=[N-].[H][H]>C(O)C.[Pd]>[N:13]1[C:14]2[C:9](=[CH:8][C:7]([C:4]([NH2:1])([CH3:5])[CH3:6])=[CH:16][CH:15]=2)[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 866592846-(2-Azidopropan-2-yl)quinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 669951062-(Quinolin-6-yl)propan-2-amineYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 6-(2-azidopropan-2-yl)quinoline (0.100 g. 2.67 mmol) in ethanol (3 ml), palladium on carbon (10 mg, 10% w/w) was added and stirred under a hydrogen atmosphere using hydrogen filled balloon. After 6 h, the reaction mass was filtered through celite, washed with methanol and concentrated to afford the title compound as brown liquid (0.079 g, 90%). 1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ8.82 (dd J=4.2, 1.6 Hz, 1H), 8.31 (d, J=8.9 Hz, 1H), 8.02 (d, J=1.9 Hz, 1H), 7.99 (dd, J=8.9, 2.1 Hz, 1H), 7.93 (d, J=8.9 Hz, 1H), 7.49 (q, J=4.2 Hz, 1H), 2.06 (s, 2H),1.46 (s, 6H).

Workup

  1. filtrationthe reaction mass was filtered through celite
  2. washwashed with methanol
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7b80f9d7dbd24c0e948e092cdcb1d23e
Source dataset
uspto-grants-2014_12
Patent number
US08912331B2

Reaction notes

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