Water → HCID 44451820, compound

HRID 750171Notes

Reaction equation

HRID 750171 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][CH3:28])[CH:14]=2)[C:9]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CI.[C:32](=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:32][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:29])[C:10]2[C:15]([C:16]=1[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[CH:14][C:13]([O:27][CH3:28])=[CH:12][CH:11]=2)=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 23060560HCID 23060560, compound

Product 1

HCID 44451820HCID 44451820, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Benzyl-6-methoxy-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid (160 mg) was dissolved in DMF (3 ml), and methyl iodide (0.06 ml) and potassium carbonate (120 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 ethyl acetate-hexane to give the title compound (120 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 ethyl acetate-hexane

Sources & evidence

ORD record
ord-a4b8cf4f31d94d79bb61e17ceac8aab0
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

Loading…