Water → HCID 46916364, compound

HRID 2045918Notes

Reaction equation

HRID 2045918 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:21]=[N:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)[CH:7]=1)=[O:4].[C-:22]#[N:23].[Na+].O>CCO>[C:22]([CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:21]=[N:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)[CH:7]=1)=[O:4])#[N:23]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 14854332-chloro-N-(3-quinoxalin-2-ylphenyl)acetamide

Product 1

HCID 46916364HCID 46916364, compoundYield 10.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-chloro-N-(3-quinoxalin-2-ylphenyl)acetamide (276 mg, 0.93 mmol) in EtOH (8 mL), NaCN (50 mg, 1.02 mmol) was added and the reaction mixture was heated at reflux for 21 hrs. After cooling to room temperature, water (10 mL) was added and the reaction mixture was extracted with ethyl acetate (20 mL). The organic phase was washed with brine (20 mL), dried over MgSO4, and the residue was purified by flash chromatography (Flash Master, 5 g Isolute Silica column, gradient 0 to 5 min hexane, then ethyl acetate up to 50% over 20 min). The isolated solid was triturated with Et2O (10 mL) and filtered to afford 2-cyano-N-[3-(quinoxalin-2-yl)phenyl]acetamide as a light-yellow solid (27 mg, 10% yield). LCMS calculated for C17H12N4O (M+H): 289.30. found 289.00. 1H-NMR (DMSO-d6, 400 Mhz) δH: 10.55 (1H, br. S), 9.52 (1H, s), 8.48 (1H, m), 8.20-8.12 (2H, m), 8.10 (1H, d, J=7 Hz), 7.98-7.80 (3H, m), 7.58 (1H, m), 3.95 (2H, s).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 21 hrs
  3. extractionthe reaction mixture was extracted with ethyl acetate (20 mL)
  4. washThe organic phase was washed with brine (20 mL)
  5. dry with materialdried over MgSO4
  6. customthe residue was purified by flash chromatography (Flash Master, 5 g Isolute Silica column, gradient 0 to 5 min hexane
  7. customThe isolated solid was triturated with Et2O (10 mL)
  8. filtrationfiltered

Sources & evidence

ORD record
ord-9eebc015f1334361a44e593057cf8fc2
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

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