Sodium Cyanide → 6-Quinoxalineacetonitrile

HRID 1505104노트

반응식

HRID 1505104 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]=[N: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)[N:6]=[CH:7][CH:8]=1

참가 물질

4

반응물 2

HCID 8929Sodium CyanideHCID 102145106-(Bromomethyl)quinoxaline

생성물 1

HCID 451217246-Quinoxalineacetonitrile수율 28.9%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
50 °C

실험 절차

To a solution of crude 6-bromomethylquinoxaline (36.0 g) in 95% ethanol (200 mL) was added NaCN (30.9 g, 0.63 mol) at room temperature. The mixture was heated at 50° C. for 3 hours and then concentrated under vacuum. Water (100 mL) and ethyl acetate (100 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 residue was purified by silica gel column (Petroleum Ether/EtOAc 10:1) to give 2-(quinoxalin-6-yl)acetonitrile (7.9 g, 23% over two steps). 1H NMR (300 MHz, CDCl3) δ 8.88-8.90 (m, 2 H), 8.12-8.18 (m, 2 H), 7.74 (dd, J=2.1, 8.7 Hz, 1 H), 4.02 (s, 2 H). MS (ESI) m/z (M+H)+ 170.0.

후처리

  1. concentrationconcentrated under vacuum
  2. additionWater (100 mL) and ethyl acetate (100 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. customThe residue was purified by silica gel column (Petroleum Ether/EtOAc 10:1)

출처 및 근거

ORD 기록
ord-bc831c92a72245389436db4fa0821d0b
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216969B2

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