Ethyl Acetate → 7-Chlorothieno[3,2-B]pyridine-2-carbonitrile

HRID 500805Notes

Reaction equation

HRID 500805 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([CH:11]=[N:12]O)[S:10][C:3]=12.CCOC(C)=O>C(OC(=O)C)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]#[N:12])[S:10][C:3]=12

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 1363351767-Chlorothieno[3,2-b]pyridine-2-carbaldehyde oxime

Product 1

HCID 222786367-Chlorothieno[3,2-B]pyridine-2-carbonitrileYield 71.1%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of the oxime 125 (100 mg, 0.47 mmol) in acetic anhydride (2 ml) was set to reflux for 3 h and then at 90° C. for 48 h. The acetic anhydride was removed under reduced pressure and the residue was partitioned between a cold aqueous K2CO3 solution and EtOAc. The organic phase was dried over anhydrous sodium sulfate, concentrated to dryness and remained solid was purified by column chromatography, eluents 25% EtOAc/hexane (25:75), then 100% EtOAc, to afford the title compound 126 (65 mg, 71% yield). MS (m/z) 195.1/197.1 (M+H).

Workup

  1. temperatureto reflux for 3 h
  2. customThe acetic anhydride was removed under reduced pressure
  3. customthe residue was partitioned between a cold aqueous K2CO3 solution and EtOAc
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. concentrationconcentrated to dryness
  6. customwas purified by column chromatography, eluents 25% EtOAc/hexane (25:75)

Sources & evidence

ORD record
ord-9894f218e2484ea2b506147bcb9ffe9f
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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