Hydrochloric Acid → 7-Chlorothieno[3,2-b]pyridine-2-carbaldehyde oxime

HRID 500804Notes

Reaction equation

HRID 500804 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([CH:11]=O)[S:10][C:3]=12.[NH2:13][OH:14].Cl>CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([CH:11]=[N:13][OH:14])[S:10][C:3]=12

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 509888497-Chlorothieno[3,2-b]pyridine-2-carbaldehyde

Product 1

HCID 1363351767-Chlorothieno[3,2-b]pyridine-2-carbaldehyde oximeYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of aldehyde 14 (scheme 3) in MeOH was added NH2OH×HCl (227 mg, 3.26 mmol) in water (0.5 mL) and the mixture was stirred at room temperature for 0.5 h. The solvents were removed by under reduced pressure and the residue was partitioned between EtOAc and water. The organic phase was dried over anhydrous sodium sulfate, filtered and evaporated to dryness to afford the title compound 125 (458 mg, 85% yield) as a white solid. MS (m/z) 213.1/215.1 (M+H).

Workup

  1. customThe solvents were removed by under reduced pressure
  2. customthe residue was partitioned between EtOAc and water
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-dd877b64733a4894aaf025a0d5b54216
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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