Sodium Cyanide → 6-Quinoxalineacetonitrile

HRID 17932

反応式

HRID 17932 の反応式
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

参加物

4

反応物 2

HCID 8929Sodium CyanideHCID 102145106-(Bromomethyl)quinoxaline

生成物 1

HCID 451217246-Quinoxalineacetonitrile収率 28.9%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
50 °C

実験手順

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, 2H), 8.12-8.18 (m, 2H), 7.74 (dd, J=2.1, 8.7 Hz, 1H), 4.02 (s, 2H). MS (ESI) m/z (M+H)+ 170.0.

後処理

  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)

出典と根拠

ORDレコード
ord-69fff797b7984ae98c1ea45ff7593871
出典データセット
uspto-grants-2010_06
特許番号
US07741321B2

関連ノート

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