Methane, dichloromethoxy- → 882023-34-9

HRID 1811409Notes

Reaction equation

HRID 1811409 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7](=[O:13])[NH:8]2.[CH3:14][O:15]C(Cl)Cl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([CH:14]=[O:15])=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7](=[O:13])[NH:8]2

Participants

5

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 129471185-Methoxy-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 86233763882023-34-9Yield 99.7%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

5-Methoxy-3,4-dihydro-1H-quinolin-2-one (5.00 g, 26 mmol) was dissolved in dichloromethane (100 ml), and dichloromethyl methyl ether (7.65 ml, 85 mmol) was added at 0° C. Titanium tetrachloride (12.4 ml, 113 mmol) was added dropwise at a temperature not higher than 10° C. Stirring was carried out at room temperature for 2 hours, and the reaction mixture was poured into ice water and separated into layers. The aqueous layer was subjected to extraction with dichloromethane. The organic layers were combined and washed twice with water, washed with a saturated sodium chloride solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was dissolved in dichloromethane, diethyl ether was added, and the produced insoluble matter was collected by filtration and dried to thereby obtain 5.32 g (yield: 92%) of 5-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-8-carboxaldehyde as a light brown powder.

Workup

  1. customseparated into layers
  2. extractionThe aqueous layer was subjected to extraction with dichloromethane
  3. washwashed 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. dissolutionThe residue was dissolved in dichloromethane
  9. additiondiethyl ether was added
  10. filtrationthe produced insoluble matter was collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-971b37cdc2cf4c2e8a9e2a726116bc50
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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