Methane, dichloromethoxy- → 6-Methoxy-2-oxo-1,2,3,4-tetrahydro-quinoline-7-carbaldehyde

HRID 1243981Notes

Reaction equation

HRID 1243981 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]2.[CH3:18][O:19]C(Cl)Cl>C(Cl)Cl.Cl>[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[CH:18]=[O:19])[NH:13][C:12](=[O:17])[CH2:11][CH2:10]2

Participants

6

Reactant 3

HCID 21004Methane, dichloromethoxy-HCID 6451240Aluminum(III) ChlorideHCID 108884676-Methoxy-1,2,3,4-tetrahydroquinolin-2-one

Product 1

HCID 101251496-Methoxy-2-oxo-1,2,3,4-tetrahydro-quinoline-7-carbaldehyde

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 0.29 gm (2.19 mmol) aluminum chloride in 5 ml of methylene chloride was prepared under nitrogen gas N2 and stirred for 15 minutes and then cooled to 0° C. The mixture was treated with 0.2 gm (1.13 mmol) 6-Methoxy-3,4-dihydro-1H-quinolin-2-one in 5 ml of methylene chloride. The reaction mixture was stirred for 10 minutes at this temperature and was then cooled to −5° C. α,α-dichloromethyl methyl ether 0.28 ml (3.07 mmol) was added over a 5 minutes period and the green reaction mixture was slowly warmed to room temperature and stirred for 6 hours. The reaction mixture was diluted with 2N HCl and extracted with methylene chloride (4×10 ml). The combined organics were dried over sodium sulfate, filtered and concentrated to yield an off white solid. The crude product was chromatographically purified on silica gel, eluting with 7/3 ethyl acetate/hexane. There was obtained 125 mg (54%) of an off white solid. MS APCI m/e 206 (p+1)

Workup

  1. customwas prepared under nitrogen gas N2
  2. stirringThe reaction mixture was stirred for 10 minutes at this temperature
  3. additionwas added over a 5 minutes period
  4. temperaturethe green reaction mixture was slowly warmed to room temperature
  5. stirringstirred for 6 hours
  6. extractionextracted with methylene chloride (4×10 ml)
  7. dry with materialThe combined organics were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto yield an off white solid
  11. customThe crude product was chromatographically purified on silica gel
  12. washeluting with 7/3 ethyl acetate/hexane
  13. customThere was obtained 125 mg (54%) of an off white solid

Sources & evidence

ORD record
ord-c253ad35e5bb4e8bab217903d5ef3eb6
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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