Methyl iodide → HCID 19045327, compound

HRID 1781432Notes

Reaction equation

HRID 1781432 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C:7]2([CH2:14][C:13](=[O:15])[C:12]3[C:16]([OH:23])=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=[CH:19][C:11]=3[O:10]2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[C:24](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[C:1]([N:4]1[CH2:5][CH2:6][C:7]2([CH2:14][C:13](=[O:15])[C:12]3[C:16]([O:23][CH3:24])=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=[CH:19][C:11]=3[O:10]2)[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 19045545HCID 19045545, compound

Product 1

HCID 19045327HCID 19045327, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1'-acetyl-3,4-dihydro-5-hydroxy-6-nitro-spiro[2H-1-benzopyran-2,4'-piperidine]-4-one (3.84 g, 12 mmol), potassium carbonate (1.66 g, 12 mmol) and methyl iodide (3.74 ml, 8.51 g, 60 mmol) in DMF (30 ml) was stirred in a sealed vessel at room temperature for 3 days, adding further portions of methyl iodide (1 ml) after 24 and 48 h. The solvent was evaporated under reduced pressure, water (60 ml) was added, the pH was adjusted to 6.5 with HCl-H2O (2M) and the mixture was extracted with methylene chloride (3×60 ml). The combined organic fractions were dried (Na2SO4) and evaporated under reduced pressure. The crude product was re-subjected to the above procedure, the solvent was evaporated under reduced pressure, water (60 ml) was added and the mixture was extracted with methylene chloride (3×60 ml). The combined organic fractions were dried (Na2SO4) and evaporated under reduced pressure to give the ketone (4.08 g) as a yellow solid, m.p. 160°-165° C.

Workup

  1. customThe solvent was evaporated under reduced pressure, water (60 ml)
  2. additionwas added
  3. extractionthe mixture was extracted with methylene chloride (3×60 ml)
  4. dry with materialThe combined organic fractions were dried (Na2SO4)
  5. customevaporated under reduced pressure
  6. customthe solvent was evaporated under reduced pressure, water (60 ml)
  7. additionwas added
  8. extractionthe mixture was extracted with methylene chloride (3×60 ml)
  9. dry with materialThe combined organic fractions were dried (Na2SO4)
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8c23b8e3f3294e6386da0a6c88fc0ae2
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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