Methyl iodide → HCID 20323738, compound

HRID 839586Notes

Reaction equation

HRID 839586 reaction equation
[C:1]([N:3]1[CH2:8][C:7]2[C:9]3[C:18]([OH:19])=[CH:17][C:16]([CH:20]([CH3:28])[CH:21]([CH3:27])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:15][C:10]=3[O:11][C:12]([CH3:14])([CH3:13])[C:6]=2[CH2:5][CH2:4]1)#[N:2].IC.[C:31](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([N:3]1[CH2:8][C:7]2[C:9]3[C:18]([O:19][CH3:31])=[CH:17][C:16]([CH:20]([CH3:28])[CH:21]([CH3:27])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:15][C:10]=3[O:11][C:12]([CH3:14])([CH3:13])[C:6]=2[CH2:5][CH2:4]1)#[N:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 20323749HCID 20323749, compound

Product 1

HCID 20323738HCID 20323738, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2.3 g (0.006 mole) of 2-cyano-5,5-dimethyl-8-(1,2-dimethylheptyl)-10-hydroxy-1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-d]pyridine, 2.8 g (0.02 mole) of iodomethane and 10 g (0.0725 mole) of potassium carbonate in anhydrous acetone was heated at reflux, with stirring, for 7 hours. After cooling, the solid was removed by filtration and discarded, and the mother liquor was concentrated on a rotary evaporator. The residual material was taken up in diethyl ether (70 ml) and washed with water, 1N HCl, and again with water. The organic layer was dried over sodium sulfate, filtered and concentrated to give 1.84 g (78%) of 2-cyano-5,5-dimethyl-8-(1,2-dimethylheptyl)-10-methoxy-1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-d]pyridine as a yellow oil. The ir and nmr spectra confirmed the structure. The compound appeared pure by thin-layer chromatography (silica gel, chloroform solvent system).

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. temperatureAfter cooling
  4. customthe solid was removed by filtration
  5. concentrationthe mother liquor was concentrated on a rotary evaporator
  6. washwashed with water, 1N HCl
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b7c2bbf619774f7e8ddd37a807fd8543
Source dataset
uspto-grants-1978_06
Patent number
US04096265

Reaction notes

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