Water → HCID 12346215, compound

HRID 1655025Notes

Reaction equation

HRID 1655025 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:8][C:9](=O)[NH:10]2)=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 7227187-methoxy-4-phenyl-quinolin-2-olHCID 21226445Aluminium lithium hydride

Product 1

HCID 12346215HCID 12346215, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 7-methoxy-4-phenyl-2-quinolinone (4.1 g) in THF (300 mL) at reflux was added lithium aluminum hydride (1M in THF; 65 mL). The mixture was refluxed for 50 hr, cooled to 0° C. and then treated successively with H2O (2.5 mL), 15% aq. NaOH (2.5 mL) and H2O (7.5 mL). The precipitate that formed was removed by filtration, washed with THF, and the filtrate was concentrated and redissolved in acetonitrile (100 mL). To this solution at r.t. was added dropwise a solution of ceric ammonium nitrate (7.7 g) in H2O (30 mL). After the addition was complete, H2O (600 mL) was added and the resulting mixture extracted with EtOAc (3×). The combined organics were washed with H2O (2×) and brine, dried (MgSO4) and concentrated. Flash chromatography of the residue (silica gel; EtOAc/hexane (1:1)) provided the title compound as a beige gum.

Workup

  1. temperatureThe mixture was refluxed for 50 hr
  2. customThe precipitate that formed
  3. customwas removed by filtration
  4. washwashed with THF
  5. concentrationthe filtrate was concentrated
  6. dissolutionredissolved in acetonitrile (100 mL)
  7. additionTo this solution at r.t. was added dropwise a solution of ceric ammonium nitrate (7.7 g) in H2O (30 mL)
  8. additionAfter the addition
  9. additionH2O (600 mL) was added
  10. extractionthe resulting mixture extracted with EtOAc (3×)
  11. washThe combined organics were washed with H2O (2×) and brine
  12. dry with materialdried (MgSO4)
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-ea79ecb101e84ac897de2165f023b30f
Source dataset
uspto-grants-1995_04
Patent number
US05410054

Reaction notes

Loading…