Methyl iodide → Ammonium Hydroxide

HRID 2374162Notes

Reaction equation

HRID 2374162 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[N:10][C:3]=12.[OH-:11].[K+].I[CH3:14]>CC(C)=O>[NH4+:5].[OH-:11].[CH3:14][N:8]1[C:4]2=[N:5][CH:6]=[CH:7][C:2]([CH3:1])=[C:3]2[N:10]=[CH:9]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 178428360HCID 178428360, compound

Product 2

HCID 14923Ammonium HydroxideHCID 21050405HCID 21050405, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

7-Methyl-3H-imidazo[4,5-b]pyridine (2.0 g, 15 mmol) was dissolved in acetone (60 ml) and treated with freshly ground KOH (4.21 g) followed by dropwise addition of iodomethane (10 ml). After 10 min, the reaction mixture was poured into satd. aq. NaHCO3 (25 ml) in water (25 ml) and extracted with DCM (4×80 ml). The organic layers were combined and dried over Na2SO4, filtered, and concentrated. SGC (DCM:MeOH:NH4OH =96:4:1 as eluant) yielded 3,7-dimethyl-3H-imidazo[4,5-b]pyridine (1.05 g). 1H NMR (CDCl3) δ 7.94 (s, 1H), 7.83 (d, 1H), 6.48 (s, 1H), 3.04 (s, 3H), 2.07 (s, 3H).

Workup

  1. additionthe reaction mixture was poured into satd
  2. extractionaq. NaHCO3 (25 ml) in water (25 ml) and extracted with DCM (4×80 ml)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1b2732c553194e2f9d21c71109cc6147
Source dataset
uspto-grants-2008_12
Patent number
US07462600B2

Reaction notes

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