Sodium Sulfate → Ethyl 7-fluoro-3-(1-methyl-1H-1,2,4-triazol-5-yl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 1968159Notes

Reaction equation

HRID 1968159 reaction equation
[CH:1](=[N:8]/[C:9]1[CH:17]=[C:16]([F:18])[CH:15]=[C:14]2[C:10]=1[CH2:11][O:12][C:13]2=[O:19])\[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-]S([O-])=O.[Na+].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+].[CH3:33][N:34]1[C:38]([CH:39]=O)=[N:37][CH:36]=[N:35]1.[CH3:41][CH2:42][O-:43].[Na+]>C(OCC)(=O)CC>[F:18][C:16]1[CH:15]=[C:14]([C:13]([O:12][CH2:11][CH3:10])=[O:19])[C:41]2[C:42](=[O:43])[CH:39]([C:38]3[N:34]([CH3:33])[N:35]=[CH:36][N:37]=3)[CH:1]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[NH:8][C:9]=2[CH:17]=1

Participants

7

Reactant 5

HCID 24436Sodium SulfateHCID 24437Sodium SulfiteHCID 2723922Sodium ethoxideHCID 136242781-methyl-1H-1,2,4-triazole-5-carbaldehydeHCID 178519071HCID 178519071, compound

Product 1

HCID 67260859Ethyl 7-fluoro-3-(1-methyl-1H-1,2,4-triazol-5-yl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylateYield 10%

Reagents, catalysts & solvents 1

HCID 7749Ethyl PropionateSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of (E)-4-(benzylideneamino)-6-fluoroisobenzofuran-1(3H)-one (1.25 g, 4.9 mmol), anhydrous Na2SO3 (1.24 g, 9.82 mmol), anhydrous Na2SO4 (2 g, 14.7 mmol) and 1-methyl-1H-1,2,4-triazole-5-carbaldehyde (900 mg, 8.1 mmol) in ethyl propionate (50 mL) was added EtONa [(sodium 316 mg, 13.8 mmol) in 25 mL ethanol] at 40° C., then the mixture was stirred at 40° C. for 3 hr. The resulting mixture was evaporated under reduced pressure, extracted with ethyl acetate (100 mL×4) and concentrated to dryness. The crude product was purified by column chromatography (silica gel, dichloromethane:methanol=200:1 to 50:1) to obtain the title compound as a green solid (190 mg, yield 10%). LC-MS (ESI) m/z: 395 (M+1)+.

Workup

  1. customThe resulting mixture was evaporated under reduced pressure
  2. extractionextracted with ethyl acetate (100 mL×4)
  3. concentrationconcentrated to dryness
  4. customThe crude product was purified by column chromatography (silica gel, dichloromethane:methanol=200:1 to 50:1)

Sources & evidence

ORD record
ord-10e7d97185a14d34a20544ac1cc4abb9
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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