Water → HCID 67397893, compound

HRID 869675Notes

Reaction equation

HRID 869675 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C:8]1[C:9]([C:18]([O:20]CC)=O)=[N:10][C:11]2[C:16]([N:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2.[C:23](#[N:25])[CH3:24].O>C1(C)C=CC=CC=1>[CH3:7][C:8]1[C:9]([C:18](=[O:20])[CH2:24][C:23]#[N:25])=[N:10][C:11]2[C:16]([N:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 589024ethyl 3-methylquinoxaline-2-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 67397893HCID 67397893, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of potassium tert-butoxide (72.7 g, 647 mmol) in toluene (810 mL) was added a solution of ethyl 3-methylquinoxaline-2-carboxylate (70.0 g, 324 mmol) and acetonitrile (38.3 mL, 809 mmol) in toluene (270 mL) dropwise over 50 min at 5° C. After being stirred for 5 min at 0° C., water (585 mL) was added. The organic layer was extracted with water (100 mL) and the aqueous layer was combined and acidified to pH 3-4 with 10% aqueous hydrochloric acid. The resulting precipitate was collected and dissolved to tetrahydrofuran. And then the organic layer was dried over sodium sulfate, filtrated and concentrated in vacuo. The crude solid was purified by silica gel column chromatography (silica gel 2.2 kg, chloroform to chloroform:ethyl acetate=19:1) to give 3-(3-methylquinoxalin-2-yl)-3-oxopropanenitrile. MS (APCI): m/z 212 (M+H).

Workup

  1. extractionThe organic layer was extracted with water (100 mL)
  2. customThe resulting precipitate was collected
  3. dissolutiondissolved to tetrahydrofuran
  4. dry with materialAnd then the organic layer was dried over sodium sulfate
  5. filtrationfiltrated
  6. concentrationconcentrated in vacuo
  7. customThe crude solid was purified by silica gel column chromatography (silica gel 2.2 kg, chloroform to chloroform:ethyl acetate=19:1)

Sources & evidence

ORD record
ord-d421b106e8df4ae48f7a35dedf40c496
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

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