Water → HCID 19707336, compound

HRID 1741890Notes

Reaction equation

HRID 1741890 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6]3([CH3:15])[C:11](=[CH:12][CH2:13][C:4]=2[CH:3]=1)[NH:10][C:9](=[O:14])[CH2:8][CH2:7]3.[H-].[Na+].[CH3:20]I.O>C(COC)OC>[F:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6]3([CH3:15])[C:11](=[CH:12][CH2:13][C:4]=2[CH:3]=1)[N:10]([CH3:20])[C:9](=[O:14])[CH2:8][CH2:7]3

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19707324HCID 19707324, compound

Product 1

HCID 19707336HCID 19707336, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

8-fluoro-10b-methyl-1,2,3,4,6,10b-hexahydrobenzo[f]quinolin-3-one (1.38 g; 6mmol) was added to a suspension of NaH (475 mg; 20 mmol) in glyme (15 ml). The mixture was refluxed for 1.5 hours and cooled quickly to room temperature. Methyl iodide (15 ml) was added and the mixture refluxed for 4 hours, then allowed to cool to room temperature. After addition of water, the mixture was concentrated to near dryness. The residue was partitioned between ethyl acetate and water. The organic layer was washed three times with water, dried over MgSO4 and concentrated under vacuum. Recrystallization from hexane afforded 737 mg (56% yield) of the subtitle compound. Melting point 110°-111° C.

Workup

  1. temperatureThe mixture was refluxed for 1.5 hours
  2. temperaturethe mixture refluxed for 4 hours
  3. temperatureto cool to room temperature
  4. concentrationthe mixture was concentrated
  5. customThe residue was partitioned between ethyl acetate and water
  6. washThe organic layer was washed three times with water
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated under vacuum
  9. customRecrystallization from hexane

Sources & evidence

ORD record
ord-e3c46cd704df42a7a34bc912cb33b33f
Source dataset
uspto-grants-1994_08
Patent number
US05334767

Reaction notes

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