Ethanol → Ethyl 2-(4-fluorophenyl)-4-oxo-3-(1,4,5-trimethyl-1H-imidazol-2-yl)-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 1467645Notes

Reaction equation

HRID 1467645 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5](/[CH:6]=[N:7]/[C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH2:10][O:11][C:12]3=[O:17])=[CH:4][CH:3]=1.[CH3:20][N:21]1[C:25]([CH3:26])=[C:24]([CH3:27])[N:23]=[C:22]1[CH:28]=O.[O-:30][CH2:31][CH3:32].[Na+].C(O)C>C(OCC)(=O)CC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]2[CH:28]([C:22]3[N:21]([CH3:20])[C:25]([CH3:26])=[C:24]([CH3:27])[N:23]=3)[C:31](=[O:30])[C:32]3[C:13]([C:12]([O:11][CH2:10][CH3:9])=[O:17])=[CH:14][CH:15]=[CH:16][C:8]=3[NH:7]2)=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 186124001,4,5-Trimethyl-1H-imidazole-2-carbaldehydeHCID 178519076HCID 178519076, compound

Product 1

HCID 67386337Ethyl 2-(4-fluorophenyl)-4-oxo-3-(1,4,5-trimethyl-1H-imidazol-2-yl)-1,2,3,4-tetrahydroquinoline-5-carboxylateYield 18%

Reagents, catalysts & solvents 1

HCID 7749Ethyl PropionateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of compound (E)-4-(4-fluorobenzylideneamino)isobenzofuran-1(3H)-one (510 mg, 2.0 mmol) and 1,4,5-trimethyl-1H-imidazole-2-carbaldehyde (304 mg, 2.2 mmol) in ethyl propionate (20 mL) was cooled to 0° C. Then a solution of sodium ethoxide in ethanol (sodium (184 mg, 8.0 mmol) in ethanol (10 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 under reduced pressure. The residue was dissolved in water and extracted with ethyl acetate (100 mL×3), then the extraction was washed with water, brine and evaporated, the crude product was purified by chromatography to obtain a yellow solid (150 mg, yield: 18%). LC-MS (ESI) m/z: 421 (M+1)+.

Workup

  1. additionAfter the addition
  2. customThe mixture was quenched with water (20 mL) and solvent
  3. customwas removed under reduced pressure
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted with ethyl acetate (100 mL×3)
  6. extractionthe extraction
  7. washwas washed with water, brine
  8. customevaporated
  9. customthe crude product was purified by chromatography

Sources & evidence

ORD record
ord-d2c53fef456a42449ca06bc5a104227b
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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