Methanol → Ethyl 2-(4-((dimethylamino)methyl)phenyl)-4-oxo-3-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 1968137Notes

Reaction equation

HRID 1968137 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].[F:23][C:24]([F:34])([F:33])[C:25]1[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=1.[O-:35][CH2:36][CH3:37].[Na+].CO>C(OCC)(=O)CC>[CH3:3][N:2]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([CH:9]2[CH:29]([C:28]3[CH:31]=[CH:32][C:25]([C:24]([F:34])([F:33])[F:23])=[CH:26][CH:27]=3)[C:13](=[O:14])[C:12]3[C:16]([C:15]([O:35][CH2:36][CH3:37])=[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 887MethanolHCID 679964-(Trifluoromethyl)benzaldehydeHCID 2723922Sodium ethoxideHCID 178483208HCID 178483208, compound

Product 1

HCID 67386466Ethyl 2-(4-((dimethylamino)methyl)phenyl)-4-oxo-3-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroquinoline-5-carboxylateYield 16%

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 (541 mg, 1.84 mmol) and 4-(trifluoromethyl)benzaldehyde (320 mg, 1.84 mmol) in anhydrous ethyl propionate (25 mL) was cooled to 0° C. Then sodium ethoxide in methanol solution (sodium (127 mg, 5.51 mmol) in anhydrous ethanol (10 mL)) was added dropwise and the mixture was stirred at 25° C. for 4 hr. The resulting mixture was quenched with water (5 mL), and then evaporated the solvents off under reduced pressure. The residue was extracted with ethyl acetate (100 mL×3) and the combined organic layers were dried over anhydrous sodium sulfate and concentrated to give crude product, which was purified by column chromatography (silica gel, dichloromethane to dichloromethane/methanol=30:1) to give the title compound (150 mg, yield 16%) as a yellow solid. LC-MS (ESI) m/z: 497 (M+1)+.

Workup

  1. customThe resulting mixture was quenched with water (5 mL)
  2. customevaporated the solvents off under reduced pressure
  3. extractionThe residue was extracted with ethyl acetate (100 mL×3)
  4. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto give crude product, which
  7. customwas purified by column chromatography (silica gel, dichloromethane to dichloromethane/methanol=30:1)

Sources & evidence

ORD record
ord-b6cb5f64210b4fc88c81ba22abdc23db
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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