Methyl iodide → HCID 86757136, compound

HRID 1384281Notes

Reaction equation

HRID 1384281 reaction equation
[OH:1][N:2]=[C:3]1[C:8]2=[N:9][C:10]([CH3:17])=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:12]=[C:7]2[CH2:6][CH2:5][CH2:4]1.[CH2:18]1COCC1.[H-].[Na+].CI>C(OCC)(=O)C.O.CN(C)C=O>[CH3:18][O:1][N:2]=[C:3]1[C:8]2=[N:9][C:10]([CH3:17])=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:12]=[C:7]2[CH2:6][CH2:5][CH2:4]1

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 136364218HCID 136364218, compound

Product 1

HCID 86757136HCID 86757136, compoundYield 74.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In an atmosphere of argon, methyl 8-hydroxyimino-2-methyl-5,6,7,8-tetrahydrocyclohexa[b]pyridine-3-carboxylate (1.01 g, 4.33 mmol) was suspended in a mixed solution of THF (5.0 ml) and dimethylformamide (DMF) (1.5 ml) at 0° C., and the suspension was mixed with sodium hydride (192.0 mg, 4.80 mmol) and stirred at room temperature for 1.5 hours. To this was added dropwise methyl iodide (192.0 mg, 4.80 mmol) at room temperature, followed by 2 hours of stirring. The reaction solution was diluted with ethyl acetate, mixed with water and then extracted with ethyl acetate. The thus obtained organic layer was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (ethyl acetate:hexane=1:3) to obtain the title compound (801.4 mg, 74.5%) as pale yellow powder.

Workup

  1. waitfollowed by 2 hours
  2. stirringof stirring
  3. extractionextracted with ethyl acetate
  4. washThe thus obtained organic layer was washed with water and saturated brine in that order
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe resulting residue was purified by a silica gel column chromatography (ethyl acetate:hexane=1:3)

Sources & evidence

ORD record
ord-e4816a3fe4234ee1a862b116e0f2bfd3
Source dataset
uspto-grants-2001_07
Patent number
US06258829B1

Reaction notes

Loading…