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

HRID 449249노트

반응식

HRID 449249 반응식
[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]

참가 물질

3

반응물 2

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

생성물 1

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

실험 절차

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): δ 8.90 (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).

후처리

  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

출처 및 근거

ORD 기록
ord-3c9a5068ba77442abd4f3849c8c0c7c1
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481739B2

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