Water → HCID 69155553, compound

HRID 750172Notes

Reaction equation

HRID 750172 reaction equation
[CH2:1]([N:8]1[C:17]([C:18]([OH:20])=[O:19])=[C:16]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:14]=2)[C:9]1=[O:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CI.[C:38](=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:38][O:19][C:18]([C:17]1[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9](=[O:35])[C:10]2[C:15]([C:16]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:14][C:13]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[CH:12][CH:11]=2)=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 23060716HCID 23060716, compound

Product 1

HCID 69155553HCID 69155553, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Benzyl-6-benzyloxy-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid (150 mg) was dissolved in DMF (3 ml) and methyl iodide (0.04 ml) and potassium carbonate (90 mg) were added at room temperature. The mixture was stirred for 12 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine. The solvent was dried over anhydrous sodium sulfate and evaporated under reduced pressure, and the obtained residue was crystallized from hexane to give the title compound (140 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialThe solvent was dried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customthe obtained residue was crystallized from hexane

Sources & evidence

ORD record
ord-d04f2afc344242008c5241796731d048
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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