Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 86613919, compound

HRID 1811406Notes

Reaction equation

HRID 1811406 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:47])[N:28]2[CH2:35][C:36]1[CH:37]=[N:38][C:39]([C:42]2[CH:46]=[CH:45][S:44][CH:43]=2)=[CH:40][CH:41]=1>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]([C:42]4[CH:46]=[CH:45][S:44][CH:43]=4)=[CH:40][CH:41]=3)[C:27](=[O:47])[CH2:26][CH2:25][C:24]=2[C:23]([CH:19]=[O:18])=[CH:32][CH:31]=1

Participants

5

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 66596896HCID 66596896, compound

Product 1

HCID 86613919HCID 86613919, compoundYield 111.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Pyridinium p-toluenesulfonate (PPTS) (0.24 g) was added to a mixed solution of 5-(1,3-dioxolan-2-yl)-8-methoxy-1-(6-thiophen-3-ylpyridin-3-ylmethyl)-3,4-dihydro-1H-quinolin-2-one (0.4 g) in acetone (8 ml) and water (4 ml), followed by heating under reflux 1.5 hours. The resulting mixture was concentrated under reduced pressure, subjected to extraction with dichloromethane, washed with water, washed with a saturated sodium chloride solution, dried over sodium sulfate, filtrated, and concentrated under reduced pressure to thereby obtain 0.4 g (yield: quantitative) of 8-methoxy-1-(6-thiophen-3-ylpyridin-3-ylmethyl)-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde as a light brown amorphous solid.

Workup

  1. temperatureby heating
  2. temperatureunder reflux 1.5 hours
  3. concentrationThe resulting mixture was concentrated under reduced pressure
  4. extractionsubjected to extraction with dichloromethane
  5. washwashed with water
  6. washwashed with a saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltrated
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b743a8915bd7485fa4e97521a51eb6da
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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