Water → 2,3-dimethyl-6-methoxy4-phenyl-2H-isoquinolin-1-one

HRID 985150Notes

Reaction equation

HRID 985150 reaction equation
[CH2:1]([C:8]1[CH:17]=C(OC)C=C[C:9]=1[C:10]([NH:12][CH3:13])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:20]([Li])[CH2:21]CC.C(Cl)(=O)C.O.[CH2:30]1[CH2:34][O:33][CH2:32][CH2:31]1>>[CH3:32][O:33][C:34]1[CH:17]=[C:8]2[C:9](=[CH:31][CH:30]=1)[C:10](=[O:11])[N:12]([CH3:13])[C:20]([CH3:21])=[C:1]2[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 225559272-Benzyl-4-methoxy-N-methylbenzamideHCID 178418339Butyllithium

Product 1

HCID 225559912,3-dimethyl-6-methoxy4-phenyl-2H-isoquinolin-1-one

Procedure

To a solution of 11 (5.00 g, 19.6 mmol) in THF under Argon at −70° C. was added n-butyllithium (18.8 mL, 2.5M). After 0.5 h acetyl chloride (2.10 mL, 29.4 mmol) was added. Stirred 0.5 h then added water and warmed to room temperature. Removed the solvent in vacuo and added 1N hydrochloric acid. Extracted with ethyl acetate (4×) and dried the combined organic portions with magnesium sulfate (anh.). Removal of the solvent in vacuo followed by trituration with ether gave 12 as a light solid (2.54 g, 9.10 mmol, 46.4%).

Workup

  1. customRemoved the solvent in vacuo
  2. additionadded 1N hydrochloric acid
  3. extractionExtracted with ethyl acetate (4×)
  4. dry with materialdried the combined organic portions with magnesium sulfate (anh.)
  5. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-c88c1e3a25894a698eae3f04fd6c5731
Source dataset
uspto-grants-2005_03
Patent number
US06870055B2

Reaction notes

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