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

HRID 1955005Notes

Reaction equation

HRID 1955005 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

15.0 g of sodium iodide and 31.0 g of sodium carbonate are added at RT to a solution of 8-amino-2,3-dimethylimidazo[1,2-a]pyridine (14.7 g) and 6-methyl-2-nitrobenzyl chloride (18.6 g) in 100 ml of acetone and the mixture is then heated at boiling under reflux for 6 h. After cooling the solution to RT and concentrating, the residue is dissolved in a mixture of 200 ml of ethyl acetate and 200 ml of water and the organic phase is separated off. After three further extractions with 100 ml of ethyl acetate each, the combined organic phases are dried over magnesium sulfate and then concentrated to 80 ml. 12.1 g of the title compound crystallize as a slightly yellow solid. The mother liquor is concentrated. Chromatographic purification of the residue on silica gel (eluent: toluene/dioxane=6:1) gives a further 14 g of the crystalline product. Recrystallization of both fractions from ethyl acetate gives 21.5 g (76%) of the title compound of m.p. 160-162° C.

Workup

  1. temperaturethe mixture is then heated
  2. temperatureunder reflux for 6 h
  3. concentrationconcentrating
  4. dissolutionthe residue is dissolved in a mixture of 200 ml of ethyl acetate and 200 ml of water
  5. customthe organic phase is separated off
  6. extractionAfter three further extractions with 100 ml of ethyl acetate each, the combined organic phases
  7. dry with materialare dried over magnesium sulfate
  8. concentrationconcentrated to 80 ml
  9. custom12.1 g of the title compound crystallize as a slightly yellow solid
  10. concentrationThe mother liquor is concentrated
  11. customChromatographic purification of the residue on silica gel (eluent: toluene/dioxane=6:1)

Sources & evidence

ORD record
ord-8be93a6de03843f3865b4e73ac78d1a8
Source dataset
uspto-grants-2000_09
Patent number
US06124313

Reaction notes

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