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

HRID 503986Notes

Reaction equation

HRID 503986 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]([CH3:13])[C:10](=[O:14])[CH2:9][CH2:8]2.[CH3:15][O:16]C(Cl)Cl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[C:12]2[N:11]([CH3:13])[C:10](=[O:14])[CH2:9][CH2:8][C:7]=2[C:6]([CH:15]=[O:16])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 21004Methane, dichloromethoxy-2×HCID 133841968-methoxy-1-methyl-3,4-dihydro-1H-quinolin-2-one

Product 1

HCID 866139148-Methoxy-1-methyl-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehydeYield 80%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

8-Methoxy-1-methyl-3,4-dihydro-1H-quinolin-2-one (1.5 g) was dissolved in dichloromethane (15 ml), and dichloromethyl methyl ether (0.86 ml) was added at room temperature, followed by cooling with ice water. Titanium tetrachloride (10.5 ml) was added dropwise, and the resulting mixture was stirred at room temperature overnight. Further, dichloromethyl methyl ether (1.29 ml) and titanium tetrachloride (15.8 ml) were added, and stirring was carried out at room temperature for 5 hours. 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. Hexane was added to the residue, and the produced insoluble matter was collected by filtration and dried to thereby obtain 1.37 g (yield: 80%) of 8-methoxy-1-methyl-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde.

Workup

  1. stirringstirring
  2. waitwas carried out at room temperature for 5 hours
  3. extractionthe aqueous layer was subjected to extraction with dichloromethane
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. additionHexane was added to the residue
  8. filtrationthe produced insoluble matter was collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-89e8987d647d402aa7840a1b1285fb16
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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