Ethyl Acetate → 8-methoxy-1-[6-(N-methyl-N-phenylamino)pyridin-3-ylmethyl]-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde

HRID 1811404Notes

Reaction equation

HRID 1811404 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[O:18]1CCO[CH:19]1[C:23]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]2[C:24]=1[CH2:25][CH2:26][C:27](=[O:50])[N:28]2[CH2:35][C:36]1[CH:37]=[N:38][C:39]([N:42]([CH3:49])[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[CH:40][CH:41]=1.C(=O)([O-])O.[Na+].C(OCC)(=O)C>CC(C)=O.O>[CH3:34][O:33][C:30]1[C:29]2[N:28]([CH2:35][C:36]3[CH:37]=[N:38][C:39]([N:42]([CH3:49])[C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=4)=[CH:40][CH:41]=3)[C:27](=[O:50])[CH2:26][CH2:25][C:24]=2[C:23]([CH:19]=[O:18])=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 66596977HCID 66596977, compound

Product 1

HCID 866139188-methoxy-1-[6-(N-methyl-N-phenylamino)pyridin-3-ylmethyl]-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehydeYield 81%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Pyridinium p-toluene sulfonate (PPTS) (0.54 g) was added to a mixed solution of 5-(1,3-dioxolan-2-yl)-8-methoxy-1-[6-(N-methyl-N-phenylamino)pyridin-3-ylmethyl]-3,4-dihydro-1H-quinolin-2-one (0.95 g) in acetone (19 ml) and water (9.5 ml), followed by heating under reflux for 2 hours. An aqueous sodium hydrogencarbonate solution was added to the reaction mixture, and extraction with ethyl acetate was performed. The extract was washed twice with water, washed with a saturated sodium chloride solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1). The purified product was concentrated under reduced pressure to thereby obtain 0.69 g (yield: 81%) of 8-methoxy-1-[6-(N-methyl-N-phenylamino)pyridin-3-ylmethyl]-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde as a light yellow amorphous solid.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 2 hours
  3. washThe extract was washed twice with water
  4. washwashed with a saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1)
  9. concentrationThe purified product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-720335fd475c4053b8f4d2501f0b33e2
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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