Ethanol → Ethyl 2,3-bis(4-((dimethylamino)methyl)phenyl)-7-fluoro-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 1968096Notes

Reaction equation

HRID 1968096 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:23]=[CH:22][C:8](/[CH:9]=[N:10]/[C:11]2[CH:19]=[C:18]([F:20])[CH:17]=[C:16]3[C:12]=2[CH2:13][O:14][C:15]3=[O:21])=[CH:7][CH:6]=1)[CH3:3].[CH3:24][N:25]([CH2:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1)[CH3:26].[O-:36][CH2:37][CH3:38].[Na+].C(O)C>C(OCC)(=O)CC>[CH3:1][N:2]([CH2:4][C:5]1[CH:23]=[CH:22][C:8]([CH:9]2[CH:32]([C:31]3[CH:34]=[CH:35][C:28]([CH2:27][N:25]([CH3:24])[CH3:26])=[CH:29][CH:30]=3)[C:37](=[O:36])[C:38]3[C:16]([C:15]([O:14][CH2:13][CH3:12])=[O:21])=[CH:17][C:18]([F:20])=[CH:19][C:11]=3[NH:10]2)=[CH:7][CH:6]=1)[CH3:3]

Participants

6

Reactant 4

HCID 702EthanolHCID 1932514-DimethylaminomethylbenzaldehydeHCID 2723922Sodium ethoxideHCID 178483209HCID 178483209, compound

Product 1

HCID 67258357Ethyl 2,3-bis(4-((dimethylamino)methyl)phenyl)-7-fluoro-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylateYield 33%

Reagents, catalysts & solvents 1

HCID 7749Ethyl PropionateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (E)-4-(4-((dimethylamino)methyl)benzylideneamino)-6-fluoroisobenzofuran-1(3H)-one (1 g, 31.9 mmol) and 4-((dimethylamino) methyl)benzaldehyde (0.52 g, 31.9 mmol) in ethyl propionate (50 mL) was cooled to 0° C. Then a solution of sodium ethoxide in ethanol (sodium (220 mg, 95.8 mmol) in ethanol (20 mL)) was added dropwise. After the addition, the mixture was stirred at room temperature for 2 hr. The mixture was quenched with water (10 mL) and solvent was removed in vacuum. The residue was dissolved in water, and then extracted with ethyl acetate (100 mL×4). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give crude product, which was purified by chromatography (silica gel, dichloromethane/methanol=10:1 to 20:3) to give the title (520 mg, yield 33%). LC-MS (ESI) m/z: 503.

Workup

  1. additionAfter the addition
  2. customThe mixture was quenched with water (10 mL) and solvent
  3. customwas removed in vacuum
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted with ethyl acetate (100 mL×4)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customto give crude product, which
  10. customwas purified by chromatography (silica gel, dichloromethane/methanol=10:1 to 20:3)
  11. customto give the title (520 mg, yield 33%)

Sources & evidence

ORD record
ord-dc426b49f34f4740884bfd1b167130ed
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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