Water → HCID 69157223, compound

HRID 750168Notes

Reaction equation

HRID 750168 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]([F:27])[CH:14]=2)[C:9]1=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CI.[C:31](=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:31][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:28])[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]([F:27])=[CH:12][CH:11]=2)=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 23060561HCID 23060561, compound

Product 1

HCID 69157223HCID 69157223, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Benzyl-6-fluoro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid (400 mg) was dissolved in DMF (4 ml) and methyl iodide (0.14 ml) and potassium carbonate (300 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. The residue was crystallized from ethyl acetate-hexane to give the title compound (200 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 residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-e355fbed4f34455fb8b53a9e4f6cd253
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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