Methyl iodide → HCID 20513233, compound

HRID 904332Notes

Reaction equation

HRID 904332 reaction equation
[C:1]([O:9][CH:10]1[CH2:19][CH2:18][C:17]2[NH:16][C:15](=[O:20])[CH2:14][CH2:13][C:12]=2[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21]I.[H-].[Na+]>O1CCCC1>[CH3:21][N:16]1[C:17]2[CH2:18][CH2:19][CH:10]([O:9][C:1](=[O:8])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:11][C:12]=2[CH2:13][CH2:14][C:15]1=[O:20]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydride2×HCID 12902700HCID 12902700, compound

Product 1

HCID 20513233HCID 20513233, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

46.5 g. of the isomer mixture containing about 60 percent of 6-benzoyloxy-3,4,5,6,7,8-hexahydro-1H-quinoline-2-one and 40% of the 3,4,4a,5,6,7-hexahydro isomer were dissolved in 400 ml. of tetrahydrofuran (THF). 80 ml. of methyl iodide were added and the resulting mixture cooled in an ice-water bath. 9.6 g. of sodium hydride (as a 50 percent suspension in mineral oil) were added in portions. After all of the sodium hydride suspension had been added, the cooling bath was removed and the reaction mixture stirred at ambient temperature under a nitrogen atmosphere for about 4 hours. The reaction mixture was then diluted with water and the aqueous mixture thoroughly extracted with chloroform. The chloroform extracts were combined and the combined extracts washed with saturated aqueous sodium chloride and then dried. The chloroform was removed by evaporation to dryness in vacuo leaving as a residue an orange oil weighing 47.3 g. Crystallization of the residue from an ether-hexane solvent mixture yielded crystals of 1-methyl-6-benzoyloxy-3,4,5,6,7,8-hexahydro-2(1H)-quinolinone and the corresponding 3,4,4a,5,6,7-hexahydro isomer.

Workup

  1. dissolutionwere dissolved in 400 ml
  2. temperaturethe resulting mixture cooled in an ice-water bath
  3. customthe cooling bath was removed
  4. additionThe reaction mixture was then diluted with water
  5. extractionthe aqueous mixture thoroughly extracted with chloroform
  6. washthe combined extracts washed with saturated aqueous sodium chloride
  7. customdried
  8. customThe chloroform was removed by evaporation to dryness in vacuo
  9. customleaving as a residue an orange oil
  10. customCrystallization of the residue from an ether-hexane solvent mixture

Sources & evidence

ORD record
ord-edc3f215c5d5474ab728293f65925e61
Source dataset
uspto-grants-1980_10
Patent number
US04230861

Reaction notes

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