Sodium Azide → 6-(2-Azidopropan-2-yl)quinoline

HRID 1404768Notes

Reaction equation

HRID 1404768 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11](O)([CH3:13])[CH3:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[N-:15]=[N+:16]=[N-:17].[Na+]>>[N:15]([C:11]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:1]=[CH:2][CH:3]=[CH:4]2)([CH3:13])[CH3:12])=[N+:16]=[N-:17]

Participants

3

Reactant 2

HCID 33557Sodium AzideHCID 669948782-(Quinolin-6-yl)propan-2-ol

Product 1

HCID 866592846-(2-Azidopropan-2-yl)quinolineYield 60%

Procedure

2-(Quinolin-6-yl)propan-2-ol (0.50 g, 2.67 mmol) and sodium azide (1.73 g, 26.70 mmol) were added successively to ice-cold trifluoroacetic acid (20 ml) and warmed to room temperature. After 12 h, the reaction mixture was cooled to 0° C., quenched with water and basified with sodium hydroxide solution and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford the title compound as brown liquid (0.340 g, 60%). 1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ8.90 (dd J=4.1, 1.6 Hz, 1H), 8.41 (d, J=7.6 Hz, 1H), 8.06 (d, J=2.1 Hz, 1H), 8.04 (d, J=9.0 Hz, 1H), 7.88 (dd, J=8.1, 2.2 Hz, 1H), 7.56 (q, J=4.2 Hz, 1H), 1.71 (s, 6H).

Workup

  1. temperaturethe reaction mixture was cooled to 0° C.
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ebdd1686db1e4aa087dd8c98dd067260
Source dataset
uspto-grants-2014_12
Patent number
US08912331B2

Reaction notes

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