Water → HCID 67395629, compound

HRID 869687Notes

Reaction equation

HRID 869687 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:13]=[C:12]2[C:7]([N:8]=[C:9]([CH3:19])[C:10]([C:14]([O:16]CC)=O)=[N:11]2)=[CH:6][CH:5]=1.[C:20](#[N:22])[CH3:21].O>C1(C)C=CC=CC=1>[F:3][C:4]1[CH:13]=[C:12]2[C:7]([N:8]=[C:9]([CH3:19])[C:10]([C:14](=[O:16])[CH2:21][C:20]#[N:22])=[N:11]2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 13197184HCID 13197184, compound

Product 1

HCID 67395629HCID 67395629, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride (60% dispersion in mineral oil, 12.0 g, 300 mmol) in toluene (450 mL) was added a solution of ethyl 7-fluoro-3-methylquinoxaline 2-carboxylate (35.1 g, 150 mmol) and acetonitrile (19.6 mL, 375 mmol) in toluene (40 mL) dropwise over 35 min at 85° C. After being stirred for 5 min at the same temperature, the reaction mixture was cooled to 0° C., and then added water (175 mL). The aqueous layer was separated and the organic layer was extracted with 1N aqueous sodium hydroxide (200 mL). The combined aqueous layer was acidified to pH 2 with conc. Hydrochloric acid (45.0 mL) at 0° C., and the resulting precipitate was collected and washed with water (150 mL). The solid was dissolved with chloroform (1000 mL) and water (500 mL). The aqueous layer was extracted with chloroform (300 mL). The combined organic layer was washed with brine, dried over sodium sulfate, filtered and the filtrate was concentrated in vacuo. The residue was triturated with ethanol to give 3-(7-fluoro-3-methylquinoxalin-2-yl)-3-oxopropanenitrile. MS (APCI): m/z 230 (M+H).

Workup

  1. customThe aqueous layer was separated
  2. extractionthe organic layer was extracted with 1N aqueous sodium hydroxide (200 mL)
  3. customwas acidified to pH 2 with conc. Hydrochloric acid (45.0 mL) at 0° C.
  4. customthe resulting precipitate was collected
  5. washwashed with water (150 mL)
  6. dissolutionThe solid was dissolved with chloroform (1000 mL) and water (500 mL)
  7. extractionThe aqueous layer was extracted with chloroform (300 mL)
  8. washThe combined organic layer was washed with brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationthe filtrate was concentrated in vacuo
  12. customThe residue was triturated with ethanol

Sources & evidence

ORD record
ord-02055d68b46947d8a16cdf31946b90eb
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

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