Methane, dichloromethoxy- → 8-Methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde

HRID 1811392Notes

Reaction equation

HRID 1811392 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[NH:11][C:10](=[O:13])[CH2:9][CH2:8]2.[CH3:14][O:15]C(Cl)Cl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[C:12]2[NH:11][C:10](=[O:13])[CH2:9][CH2:8][C:7]=2[C:6]([CH:14]=[O:15])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 133754763,4-Dihydro-8-methoxy-2(1H)-quinolinone

Product 1

HCID 859802658-Methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehydeYield 90%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

8-Methoxy-3,4-dihydro-1H-quinolin-2-one (5 g) was dissolved in dichloromethane (100 ml), and dichloromethyl methyl ether (6.4 ml) was added at room temperature, followed by cooling in an ice water bath. Titanium tetrachloride (85 ml) was added dropwise at a temperature not higher than 10° C., and the resulting mixture was stirred at room temperature overnight. The reaction mixture was poured into ice water, and the aqueous layer was subjected to extraction with dichloromethane. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. Diethyl ether was added to the residue and the produced solid was collected by filtration and dried to thereby obtain 5.2 g (yield: 90%) of 8-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde.

Workup

  1. temperatureby cooling in an ice water bath
  2. extractionthe aqueous layer was subjected to extraction with dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. additionDiethyl ether was added to the residue
  7. filtrationthe produced solid was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-07b45fe88bfd4eb8a444c1bdeaa83a49
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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