Water → HCID 22048471, compound

HRID 1830812Notes

Reaction equation

HRID 1830812 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([C:20]4[CH:24]=[CH:23][O:22][CH:21]=4)=[O:19])[CH:16]=3)[NH:11][C:10](=[O:25])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].I[CH3:29].O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([C:20]4[CH:24]=[CH:23][O:22][CH:21]=4)=[O:19])[CH:16]=3)[N:11]([CH3:29])[C:10](=[O:25])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22048467HCID 22048467, compound

Product 1

HCID 22048471HCID 22048471, compoundYield 9.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of (intermediate 26) (0.04 mol) in DMF (200 ml) was cooled to 5° C. under N2 flow. NaH 80% in oil (0.048 mol) was added portionwise. The mixture was stirred at 5° C. for 30 min. Then iodomethane (0.048 mol) was added dropwise. The mixture was stirred at 5° C. for 30 min, hydrolized and poured out into water. The precipitate was filtered off, washed with water and taken up in CH2Cl2. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated till dryness. The residue (15.5 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/EtOAc 85/15; 15–40 μm). The pure fractions were collected and the solvent was evaporated. The residue (13.3 g, 91.7%) was crystallized from CH3CN and DIPE. The precipitate was filtered off and dried, yielding 1.5 g (9.6%) of 4-(3-chlorophenyl)-6-(3-furanylcarbonyl)-1-methyl-2(1H)-quinolinone (intermediate 27), melting point 192° C.

Workup

  1. stirringThe mixture was stirred at 5° C. for 30 min
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated till dryness
  8. customThe residue (15.5 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/EtOAc 85/15; 15–40 μm)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated
  11. customThe residue (13.3 g, 91.7%) was crystallized from CH3CN and DIPE
  12. filtrationThe precipitate was filtered off
  13. customdried

Sources & evidence

ORD record
ord-69515be95c754931a985341744f715ae
Source dataset
uspto-grants-2006_06
Patent number
US07067531B2

Reaction notes

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