Pyridine → 1,2,3,4-Tetrahydro-6-methoxy-1-methyl-2-oxo-4-quinolineacetaldehyde

HRID 2372023Notes

Reaction equation

HRID 2372023 reaction equation
N1C=CC=CC=1.[OH:7][CH2:8][CH2:9][CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]([CH3:22])[C:12](=[O:23])[CH2:11]1>ClCCl.[O-2].[O-2].[O-2].[Cr+6]>[CH3:21][O:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH3:22])[C:12](=[O:23])[CH2:11][CH:10]2[CH2:9][CH:8]=[O:7]

Participants

5

Reactant 2

HCID 1049PyridineHCID 156788713,4-dihydro-4-(2-hydroxyethyl)-6-methoxy-1-methyl-2(1H)-quinolinone

Product 1

HCID 156788721,2,3,4-Tetrahydro-6-methoxy-1-methyl-2-oxo-4-quinolineacetaldehyde

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a chilled (0° C.) solution of 69 ml of pyridine in 600 ml of dichloromethane was added 42.5 g of chromium trioxide. The resulting mixture was stirred at room temperature for 0.5 hour and a solution of 10.0 g of 3,4-dihydro-4-(2-hydroxyethyl)-6-methoxy-1-methyl-2(1H)-quinolinone in 100 ml of dichloromethane was added, dropwise. The reaction mixture was stirred for 0.5 hour, the solvent was decanted, and the resulting residue washed with dichloromethane. The combined organic layers were washed with 5% sodium hydroxide solution, 10% hydrochloric acid solution, water, and brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The resulting oil was filtered through silica (elution with ethyl acetate) and concentrated to afford 1,2,3,4-tetrahydro-6-methoxy-1-methyl-2-oxo-4-quinolineacetaldehyde.

Workup

  1. stirringThe reaction mixture was stirred for 0.5 hour
  2. customthe solvent was decanted
  3. washthe resulting residue washed with dichloromethane
  4. washThe combined organic layers were washed with 5% sodium hydroxide solution, 10% hydrochloric acid solution, water, and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. filtrationThe resulting oil was filtered through silica (elution with ethyl acetate)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-fb30fae875864094b3c79691007802e5
Source dataset
uspto-grants-1992_03
Patent number
US05097033

Reaction notes

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