Water → HCID 19379420, compound

HRID 2210680Notes

Reaction equation

HRID 2210680 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[NH:9][C:8](=O)[CH:7]=2)=[CH:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[N:9]=[CH:8][CH:7]=2)=[CH:2]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 19379412HCID 19379412, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19379420HCID 19379420, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(3-furyl)-7-methoxy-2-quinolinone (4.1 g) from Step 1 in THF (250 mL) at reflux was added LiAlH4 (1M in THF; 68 mL). The mixture was refluxed for 50 hr., cooled to 0° C., and then treated successively with H2O (2.6 mL), 15% aq. NaOH (2.6 mL), and H2O (7.8 mL). The precipitate that formed was removed by filtration, washing with THF, and the tiltrate was concentrated and redissolved in MeCN (100 mL). To this solution at r.t. was added a solution of Ce(NH4)2 (NO3)6 (8.7 g) in H2O (30 mL). After the addition was complete, H2O (500 mL) was added and the resulting mixture extracted with EtOAc (3x). The combined organics were washed with H2O (2x) and brine, dried (MgSO4), and concentrated. Flash chromatography of the residue (silica gel; EtOAc/hexane (3:1)) provided 4-(3-furyl)-7-methoxyquinoline as a solid. A portion of this material (1.0 g) and pyridine hydrochloride (4 g) were heated at 175°-180° C. for 5 hr. While still hot, H2O (50 mL) and ice was added, causing the formation of a precipitate. Filtration and drying of this material provided the title compound as a solid.

Workup

  1. temperatureThe mixture was refluxed for 50 hr
  2. customThe precipitate that formed
  3. customwas removed by filtration
  4. washwashing with THF
  5. concentrationthe tiltrate was concentrated
  6. dissolutionredissolved in MeCN (100 mL)
  7. additionTo this solution at r.t. was added a solution of Ce(NH4)2 (NO3)6 (8.7 g) in H2O (30 mL)
  8. additionAfter the addition
  9. additionH2O (500 mL) was added
  10. extractionthe resulting mixture extracted with EtOAc (3x)
  11. washThe combined organics were washed with H2O (2x) and brine
  12. dry with materialdried (MgSO4)
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-354d0b5cb5994e51ab49d3e46611f969
Source dataset
uspto-grants-1995_10
Patent number
US05459271

Reaction notes

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