Hydrochloric Acid → HCID 12782121, compound

HRID 2059295Notes

Reaction equation

HRID 2059295 reaction equation
[NH:1]1[C:10]2[CH:5]([CH2:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]1=O.[H-].[Na+].S([O:19][CH3:20])(OC)(=O)=O.[OH-].[Na+].[ClH:23]>CN(C)C=O.C1(C)C=CC=CC=1.O>[Cl:23][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:1]([CH3:2])[C:20](=[O:19])[CH2:3][CH2:4]2

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 19026177HCID 19026177, compound

Product 1

HCID 12782121HCID 12782121, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21735183Dimethylformamide tolueneSolvent

Procedure

This tetrahydroquinolinone is dissolved in 100 ml of dimethylformamide/toluene (1:1); after addition of 1.8 g of sodium hydride (80% in paraffin oil), stirring is effected for 30 minutes at room temperature, followed by addition of 7.8 g of dimethyl sulphate and heating to 50° for 1 hour. After cooling of the mixture, 600 ml of water and 20 ml of 2 N sodium hydroxide solution are added; stirring is effected for 10 minutes, followed by acidification with 2 N hydrochloric acid. Extraction with ethyl acetate (4 times, with 300 ml each time), drying and concentration yield a solid residue which is recrystallised from ethyl acetate/petroleum ether (1:1) and yields 6.0 g (55% of theory) of 6-chloro-1-methyl-1,2,3,4-tetrahydroquinolin-2-one (m.p. 76°-78° C.).

Workup

  1. temperatureheating to 50° for 1 hour
  2. additionare added
  3. stirringstirring
  4. waitis effected for 10 minutes
  5. extractionExtraction with ethyl acetate (4 times, with 300 ml each time)
  6. customdrying
  7. concentrationconcentration
  8. customyield a solid residue which
  9. customis recrystallised from ethyl acetate/petroleum ether (1:1)

Sources & evidence

ORD record
ord-d346b30ebbc14efe8a27b04d5c952109
Source dataset
uspto-grants-1982_03
Patent number
US04322439

Reaction notes

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