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

HRID 1968101Notes

Reaction equation

HRID 1968101 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][N:10]([CH2:12][C:13]1[CH:31]=[CH:30][C:16](/[CH:17]=[N:18]/[C:19]2[CH:27]=[C:26]([F:28])[CH:25]=[C:24]3[C:20]=2[CH2:21][O:22][C:23]3=[O:29])=[CH:15][CH:14]=1)[CH3:11].[O-:32][CH2:33][CH3:34].[Na+].C(O)C>C(OCC)(=O)CC>[CH3:9][N:10]([CH2:12][C:13]1[CH:31]=[CH:30][C:16]([CH:17]2[CH:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:33](=[O:32])[C:34]3[C:24]([C:23]([O:22][CH2:21][CH3:20])=[O:29])=[CH:25][C:26]([F:28])=[CH:27][C:19]=3[NH:18]2)=[CH:15][CH:14]=1)[CH3:11]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 702EthanolHCID 2723922Sodium ethoxideHCID 178483209HCID 178483209, compound

Product 1

HCID 67260728Ethyl 2-(4-((dimethylamino)methyl)phenyl)-7-fluoro-4-oxo-3-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylateYield 25%

Reagents, catalysts & solvents 1

HCID 7749Ethyl PropionateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of compound benzaldehyde (75 mg, 0.705 mmol) and (E)-4-(4-((dimethylamino)methyl)benzylideneamino)-6-fluoroisobenzofuran-1(3H)-one (220 mg, 0.705 mmol) in ethyl propionate (5 mL) was cooled to 0° C. Then a solution of sodium ethoxide in ethanol (sodium (65 mg, 2.82 mmol) in ethanol (3 mL)) was added dropwise. After the addition, the mixture was stirred at room temperature for 2.5 hr. The mixture was quenched with water (20 mL) and solvent was removed in vacuum. The residue was dissolved in water and extracted with ethyl acetate for three times. The extract was washed with water and brine and then the solvent was evaporated. The crude product was purified by chromatography to obtain the title compound as a yellow solid (80 mg, yield 25%). LC-MS (ESI) m/z: 447 (M+1)+.

Workup

  1. additionAfter the addition
  2. customThe mixture was quenched with water (20 mL) and solvent
  3. customwas removed in vacuum
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted with ethyl acetate for three times
  6. washThe extract was washed with water and brine
  7. customthe solvent was evaporated
  8. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-35f8c49efe974109b2d9f61da6161613
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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