Acetone → HCID 18180279, compound

HRID 1359025Notes

Reaction equation

HRID 1359025 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]2[CH2:7][CH2:8][CH2:9][C:10](=NO)[C:11]=2[CH:12]=1.CC(C)=[O:17]>Cl>[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]2[CH2:7][CH2:8][CH2:9][C:10](=[O:17])[C:11]=2[CH:12]=1

Participants

4

Reactant 2

HCID 180AcetoneHCID 136404655HCID 136404655, compound

Product 1

HCID 18180279HCID 18180279, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 3-methoxy-7,8-dihydro-5(6H)-isoquinolinone oxime (1.20 g, 6.25 mmol) in a mixture of acetone (40 ml) and 6M hydrochloric acid (27 ml) was refluxed for 4 h then allowed to cool to room temperature. The mixture was concentrated to remove acetone then basified with sodium carbonate and extracted four times with ethyl acetate. The combined organic extracts were dried (MgSO4), concentrated and the residue subjected to column chromatography (silica, ethyl acetate-hexane, 1:4) to afford the title compound (0.81 g) as a white solid m.p. 7981°. MS (ES+) 178 (MH+).

Workup

  1. temperaturewas refluxed for 4 h
  2. concentrationThe mixture was concentrated
  3. customto remove acetone
  4. extractionextracted four times with ethyl acetate
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4aaabb76727d4d1db707c87093320956
Source dataset
uspto-grants-2003_07
Patent number
US06599908B1

Reaction notes

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