Sodium Cyanide → (Quinolin-6-yl)acetonitrile

HRID 401543

반응식

HRID 401543 반응식
Br[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.[C-:13]#[N:14].[Na+]>C(O)C>[N:9]1[C:10]2[C:5](=[CH:4][C:3]([CH2:2][C:13]#[N:14])=[CH:12][CH:11]=2)[CH:6]=[CH:7][CH:8]=1

참가 물질

4

반응물 2

HCID 8929Sodium CyanideHCID 2243966-(Bromomethyl)quinoline

생성물 1

HCID 21992552(Quinolin-6-yl)acetonitrile수율 18.3%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
50 °C

실험 절차

To a solution of crude 6-bromomethylquinoline (1.8 g) in 95% ethanol (30 mL) was added NaCN (2.0 g, 40.8 mmol) at room temperature. The mixture was heated at 50° C. for 3 hours and then concentrated under vacuum. Water (50 mL) and ethyl acetate (50 mL) were added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organics were washed with brine, dried over Na2SO4 and concentrated under vacuum. The combined crude product was purified by column (Petroleum Ether/EtOAc 5:1) to give 2-(quinolin-6-yl)acetonitrile (0.25 g, 8% over two steps). 1H NMR (300 MHz, CDCl3) δ 8.95 (dd, J=1.5, 4.2 Hz, 1H), 8.12-8.19 (m, 2H), 7.85 (s, 1H), 7.62 (dd, J=2.1, 8.7 Hz, 1H), 7.46 (q, J=4.2 Hz, 1H), 3.96 (s, 2H). MS (ESI) m/e (M+H)+169.0.

후처리

  1. concentrationconcentrated under vacuum
  2. additionWater (50 mL) and ethyl acetate (50 mL) were added
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under vacuum
  8. customwas purified by column (Petroleum Ether/EtOAc 5:1)

출처 및 근거

ORD 기록
ord-61e3d65ef972495e91d1fbde45d0cfc9
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741933B2

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