Tetrahydrofuran → HCID 22175795, compound

HRID 1797483Notes

Reaction equation

HRID 1797483 reaction equation
[CH2:1]([O:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([Cl:17])=[C:13]([Cl:16])[CH:14]=2)[C:9](=[O:18])[N:8]([CH3:19])[C:7]=1[CH:20]=[O:21])[CH2:2][CH2:3][CH3:4].O1CCC[CH2:23]1.O1CCCC1.C[Mg]Br>O>[CH2:1]([O:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([Cl:17])=[C:13]([Cl:16])[CH:14]=2)[C:9](=[O:18])[N:8]([CH3:19])[C:7]=1[CH:20]([OH:21])[CH3:23])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 22175327HCID 22175327, compoundHCID 178420675HCID 178420675, compound

Product 1

HCID 22175795HCID 22175795, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-butoxy-6,7-dichloro-2-methyl-1-oxo-1,2-dihydro-3-isoquinolinealdehyde (0.98 g, 24 mmol) in tetrahydrofuran (20 mmol) was added 3N methylmagnesium bromide tetrahydrofuran solution (1.5 ml, 4.5 mmol) at 0° C. and the obtained mixture was stirred at 0° C. for 1 h. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-n-hexane to give 4-butoxy-6,7-dichloro-3-(1-hydroxyethyl)-2-methyl-1(2H)-isoquinolinone (0.95 g, 92.2%) as crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-99f7a03fb84b4804b6781a33ebce2105
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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