Sodium Iodide → 8-(6-Methyl-2-nitrobenzylamino)-2,3-dimethylimidazo[1,2-a]pyridine

HRID 1377477Notes

Reaction equation

HRID 1377477 reaction equation
[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].[NH2:9][C:10]1[C:11]2[N:12]([C:16]([CH3:20])=[C:17]([CH3:19])[N:18]=2)[CH:13]=[CH:14][CH:15]=1.[CH3:21][C:22]1[C:27]([CH2:28]Cl)=[C:26]([N+:30]([O-:32])=[O:31])[CH:25]=[CH:24][CH:23]=1>CC(C)=O>[CH3:21][C:22]1[C:27]([CH2:28][NH:9][C:10]2[C:11]3[N:12]([C:16]([CH3:20])=[C:17]([CH3:19])[N:18]=3)[CH:13]=[CH:14][CH:15]=2)=[C:26]([N+:30]([O-:32])=[O:31])[CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 122040702-(chloromethyl)-1-methyl-3-nitroBenzeneHCID 218739802,3-Dimethylimidazo[1,2-a]pyridin-8-amine

Product 1

HCID 153824248-(6-Methyl-2-nitrobenzylamino)-2,3-dimethylimidazo[1,2-a]pyridineYield 49.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Sodium iodide (15.0 g) and sodium carbonate (31.0 g) are added to a solution of 8-amino-2,3-dimethylimidazo[1,2-a]pyridine (14.7 g) and 6-methyl-2-nitrobenzylchloride (18.6 g) in acetone (100 ml) at RT and are heated to reflux for 6 h. After cooling to RT and evaporation of the solvent, the residue is dissolved in a mixture of ethyl acetate (200 ml) and water (200 ml), and the organic phase is separated off. After three further extractions with ethyl acetate (100 ml) the combined organic layers are dried over magnesium sulfate and concentrated to a volume of 80 ml. 12.1 g of the title compound crystallize as a faintly yellow solid. The mother liquor is evaporated and the residue is purified by chromatography on silica gel (toluene/dioxane=6:1 as eluent) to yield additional 14 g of crystalline material. After recrystallization of both fractions from ethyl acetate, 21.5 g (76%) of the title compound of m.p. 160°-162° C. are isolated.

Workup

  1. temperatureare heated
  2. temperatureto reflux for 6 h
  3. customevaporation of the solvent
  4. dissolutionthe residue is dissolved in a mixture of ethyl acetate (200 ml) and water (200 ml)
  5. customthe organic phase is separated off
  6. extractionAfter three further extractions with ethyl acetate (100 ml) the combined organic layers
  7. dry with materialare dried over magnesium sulfate
  8. concentrationconcentrated to a volume of 80 ml
  9. custom12.1 g of the title compound crystallize as a faintly yellow solid
  10. customThe mother liquor is evaporated
  11. customthe residue is purified by chromatography on silica gel (toluene/dioxane=6:1 as eluent)

Sources & evidence

ORD record
ord-8cbea724bf9f43308866fc1c1827829d
Source dataset
uspto-grants-1997_09
Patent number
US05665730

Reaction notes

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