Ethanol → Ethyl 3-(4,5-dimethyl-4H-1,2,4-triazol-3-yl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 1467656Notes

Reaction equation

HRID 1467656 reaction equation
[CH:1](=[N:8]/[C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][O:12][C:13]2=[O:18])\[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][N:20]1[C:24]([CH3:25])=[N:23][N:22]=[C:21]1[CH:26]=O.[O-:28][CH2:29][CH3:30].[Na+].C(O)C>C(OCC)(=O)CC.C(OCC)(=O)C.CO>[CH3:19][N:20]1[C:24]([CH3:25])=[N:23][N:22]=[C:21]1[CH:26]1[C:29](=[O:28])[C:30]2[C:14]([C:13]([O:12][CH2:11][CH3:10])=[O:18])=[CH:15][CH:16]=[CH:17][C:9]=2[NH:8][CH:1]1[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 552536594,5-dimethyl-4H-1,2,4-triazole-3-carbaldehydeHCID 178519069HCID 178519069, compound

Product 1

HCID 67261147Ethyl 3-(4,5-dimethyl-4H-1,2,4-triazol-3-yl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylateYield 15%

Reagents, catalysts & solvents 2

HCID 7749Ethyl PropionateSolventHCID 21584119Ethylacetate methanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (E)-4-(benzylideneamino)isobenzofuran-1(3H)-one (237 mg, 1 mmol) and 4,5-dimethyl-4H-1,2,4-triazole-3-carbaldehyde (150 mg, 1.2 mmol) in ethyl propionate (10 mL) was cooled to 0° C. Then a solution of sodium ethoxide in ethanol [sodium (92 mg, 4 mmol) in ethanol (5 mL)] was added dropwise. After the addition, the mixture was stirred at 10° C. for 5 hr, then 30° C. 2.5 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 (30 mL×4). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give crude product. The crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=5:1 then ethyl acetate/methanol=15:1) to give the title compound (60 mg, yield: 15%). LC-MS (ESI) m/z: 391 (M+1)+.

Workup

  1. additionAfter the addition
  2. custom30° C
  3. custom2.5 hr
  4. customThe mixture was quenched with water (10 mL) and solvent
  5. customwas removed in vacuum
  6. dissolutionThe residue was dissolved in water
  7. extractionextracted with ethyl acetate (30 mL×4)
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated
  11. customto give crude product
  12. customThe crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=5:1

Sources & evidence

ORD record
ord-41ee42c5ddf840a0b7e1d6e13e5319bb
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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