Sodium Cyanide → 6-Quinoxalineacetonitrile

HRID 881091Notes

Reaction equation

HRID 881091 reaction equation
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

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 102145106-(Bromomethyl)quinoxaline

Product 1

HCID 451217246-QuinoxalineacetonitrileYield 28.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-eb76f3ea54344c01a2dd97bda0d47a8f
Source dataset
uspto-grants-2015_03
Patent number
US08993600B2

Reaction notes

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