Tetrahydrofuran → 7,8-Dihydro-6H-isoquinolin-5-one oxime

HRID 2265132Notes

Reaction equation

HRID 2265132 reaction equation
O1CCCC1.[CH:6]1[C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[CH:9]=[CH:8][N:7]=1.CC(C)([O-])C.[K+].[N:22](OC(C)(C)C)=[O:23]>O>[CH:6]1[C:15]2[CH2:14][CH2:13][CH2:12][C:11](=[N:22][OH:23])[C:10]=2[CH:9]=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 10906Tert-Butyl nitriteHCID 1190105,6,7,8-TetrahydroisoquinolineHCID 23665647Potassium tert-butoxide

Product 1

HCID 1357421827,8-Dihydro-6H-isoquinolin-5-one oxime

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a nitrogen atmosphere, tetrahydrofuran (125 mL) solution of 6.5 mL of 5,6,7,8-tetrahydroisoquinoline was added to tetrahydrofuran (100 mL) solution of 11.4 g of potassium tert-butoxide, and stirred at room temperature for 18 hours. Next, 17.5 mL of tert-butyl nitrite was dropwise added to the reaction liquid at 0° C., and stirred at room temperature for 18 hours. Saturated saline water was added to the reaction liquid, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was crystallized from water/ethanol to obtain 6.06 g of the entitled compound as a pale brown solid.

Workup

  1. stirringstirred at room temperature for 18 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated saline water
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe solvent was evaporated off under reduced pressure
  6. customthe residue was crystallized from water/ethanol

Sources & evidence

ORD record
ord-ff30845bda8a4c44830d9bbb5e2fb053
Source dataset
uspto-grants-2010_12
Patent number
US07855294B2

Reaction notes

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