Methyl iodide → HCID 18180140, compound

HRID 1358945Notes

Reaction equation

HRID 1358945 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1.IC.[BH4-].[Na+].[C:22](=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(O)C.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[C:12]1[CH2:13][CH2:14][N:15]([CH3:22])[CH2:16][CH:17]=1

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 4311764Sodium borohydrideHCID 144519694-(2-Methoxy-5-nitrophenyl)pyridine

Product 1

HCID 18180140HCID 18180140, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 4-(2-methoxy-5-nitrophenyl)pyridine (D36) (3.4 g, 14.8 mmol) in acetone (150 ml) was treated with excess iodomethane (5 ml) and the mixture stirred at room temperature overnight. The precipitated quaternary salt was filtered off, washed with acetone and dried, giving 5.02 g. This was dissolved in 1:1 ethanol:water (230 ml) and treated portionwise at room temperature, under argon, with sodium borohydride (1.23 g, 32.4 mmol). The mixture was stirred for 1 h at room temperature then potassium carbonate (10 g) was added and the organic layer was separated from the aqueous phase, which was back-extracted with ethyl acetate. The organic phases were combined and dried (Na2SO4) and evaporated under reduced pressure to give the title compound (D37) as an orange oil, which slowly crystallised (3.05 g, 91%).

Workup

  1. filtrationThe precipitated quaternary salt was filtered off
  2. washwashed with acetone
  3. customdried
  4. customgiving 5.02 g
  5. stirringThe mixture was stirred for 1 h at room temperature
  6. customthe organic layer was separated from the aqueous phase, which
  7. extractionwas back-extracted with ethyl acetate
  8. dry with materialdried (Na2SO4)
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1b11caaee7fd4daab2d8aa3519c7482b
Source dataset
uspto-grants-2003_07
Patent number
US06599904B2

Reaction notes

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