Methyl iodide → HCID 20515681, compound

HRID 1902530Notes

Reaction equation

HRID 1902530 reaction equation
CI.[Mg].[CH3:4][C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2.Cl.Cl[CH2:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.[Cl-].[NH4+]>CCOCC.O>[CH3:4][C:5]1[NH:6][C:7]2[C:12]([C:13]=1[CH2:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 72242-MethylindoleHCID 25517Ammonium ChlorideHCID 745704-(Chloromethyl)pyridinium chlorideHCID 5462224Magnesium

Product 1

HCID 20515681HCID 20515681, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Procedure

Methyl iodide (32.0 g) in dry ether (100 ml) was added dropwise to a stirred mixture of magnesium and dry ether (50 ml) at such a rate that the reaction was not too vigorous. After completion of the addition the mixture was heated under reflux for 30 minutes and then cooled to 0°. A solution of 2-methylindole (16.9 g) in dry ether (100 ml) was added dropwise with stirring and the resulting mixture was then heated under reflux for 1.5 hours. It was then cooled to 0° and 4-chloromethyl pyridine hydrochloride (10.5 g) was added portionwise with stirring. The mixture was heated under reflux with stirring for 3 hours and then cooled. A solution of ammonium chloride (30 g) in water (200 ml) was added dropwise with stirring and then the layers were separated. The ether layer was dried (Na2SO4) and evaporated to give an oil which was chromatographed on silica gel. Elution with chloroform initially gave some impurity together with the starting indole. Further elution gave 2-methyl-3-(4-pyridylmethyl)indole (8.0 g), m.p. 126°-127° C. (from ether).

Workup

  1. additionAfter completion of the addition the mixture
  2. temperaturewas heated
  3. temperatureunder reflux for 30 minutes
  4. temperaturecooled to 0°
  5. temperaturethe resulting mixture was then heated
  6. temperatureunder reflux for 1.5 hours
  7. temperatureIt was then cooled to 0°
  8. stirringwith stirring
  9. temperatureThe mixture was heated
  10. temperatureunder reflux
  11. stirringwith stirring for 3 hours
  12. temperaturecooled
  13. stirringwith stirring
  14. customthe layers were separated
  15. dry with materialThe ether layer was dried (Na2SO4)
  16. customevaporated
  17. customto give an oil which
  18. customwas chromatographed on silica gel
  19. washElution with chloroform

Sources & evidence

ORD record
ord-162644b01e46495d89f6a5ab4be622dc
Source dataset
uspto-grants-1982_12
Patent number
US04363912

Reaction notes

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