Ethanol → Ethyl 2-(4-((dimethylamino)methyl)phenyl)-4-oxo-3-p-tolyl-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 907999Notes

Reaction equation

HRID 907999 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:22]=[CH:21][C:8](/[CH:9]=[N:10]/[C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH2:13][O:14][C:15]3=[O:20])=[CH:7][CH:6]=1)[CH3:3].[CH3:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1.[O-:32][CH2:33][CH3:34].[Na+].C(O)C>C(OCC)(=O)CC>[CH3:3][N:2]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([CH:9]2[CH:23]([C:24]3[CH:31]=[CH:30][C:27]([CH3:28])=[CH:26][CH:25]=3)[C:13](=[O:14])[C:12]3[C:16]([C:15]([O:32][CH2:33][CH3:34])=[O:20])=[CH:17][CH:18]=[CH:19][C:11]=3[NH:10]2)=[CH:21][CH:22]=1)[CH3:1]

Participants

6

Reactant 4

HCID 702EthanolHCID 77254-MethylbenzaldehydeHCID 2723922Sodium ethoxideHCID 178483208HCID 178483208, compound

Product 1

HCID 67259015Ethyl 2-(4-((dimethylamino)methyl)phenyl)-4-oxo-3-p-tolyl-1,2,3,4-tetrahydroquinoline-5-carboxylateYield 15%

Reagents, catalysts & solvents 1

HCID 7749Ethyl PropionateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (E)-4-(4-((dimethylamino)methyl)benzylideneamino)isobenzofuran-1(3H)-one (500 mg, 1.7 mmol) and 4-methylbenzaldehyde (204 mg, 1.7 mmol) in ethyl propionate (30 mL) was cooled to 0° C. Then a solution of sodium ethoxide in ethanol (sodium (156 mg, 6.8 mmol) in ethanol (30 mL)) was added dropwise. After the addition, the mixture was stirred at 10° C. for 1 hr, then at 30° C. for 3 hr. The mixture was quenched with water (30 mL) and solvent was removed in vacuum. The residue was dissolved in water, and then extracted with ethyl acetate (30 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=100:1 to 10:1) to give the title compound (110 mg, yield: 15%). LC-MS (ESI) m/z: 443 (M+1)+.

Workup

  1. additionAfter the addition
  2. waitat 30° C. for 3 hr
  3. customThe mixture was quenched with water (30 mL) and solvent
  4. customwas removed in vacuum
  5. dissolutionThe residue was dissolved in water
  6. extractionextracted with ethyl acetate (30 mL×4)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customto give crude product, which
  11. customwas purified by chromatography (silica gel, dichloromethane/methanol=100:1 to 10:1)

Sources & evidence

ORD record
ord-23a225ee02b945fb90bca7c433107345
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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