Sodium Iodide → 8-(2-Nitro-6-methylbenzylamino)-3-chloro-2-methylimidazo[1,2-a]pyridine

HRID 1955006Notes

Reaction equation

HRID 1955006 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([Cl:11])=[CH:9][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:12][C:13]1[C:18]([CH2:19]Cl)=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=[CH:15][CH:14]=1.[C:24](=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>CC(C)=O>[Cl:11][C:8]1[N:4]2[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][CH2:19][C:18]3[C:13]([CH3:12])=[CH:14][CH:15]=[CH:16][C:17]=3[N+:21]([O-:23])=[O:22])[C:3]2=[N:10][C:9]=1[CH3:24]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 122040702-(chloromethyl)-1-methyl-3-nitroBenzeneHCID 232941763-Chloroimidazo[1,2-a]pyridin-8-amine

Product 1

HCID 232941638-(2-Nitro-6-methylbenzylamino)-3-chloro-2-methylimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Starting from 8-amino-3-chloroimidazo[1,2-a]pyridine (9.26 g), 6-methyl-2-nitrobenzyl chloride (10.5 g), sodium carbonate (13.7 g) and sodium iodide (8.55 g) in acetone (380 ml) according to the procedure indicated in Example B1 gives, after chromatography on silica gel (eluent: toluene/dioxane=20:1) and crystallization from ethyl acetate/cyclohexane, 10.6 g (63%) of the title compound of m.p. 142-144° C.

Workup

  1. customgives
  2. customafter chromatography on silica gel (eluent: toluene/dioxane=20:1) and crystallization from ethyl acetate/cyclohexane, 10.6 g (63%) of the title compound of m.p. 142-144° C.

Sources & evidence

ORD record
ord-b7262dd9aca44a7d84425fd8463c6f78
Source dataset
uspto-grants-2000_09
Patent number
US06124313

Reaction notes

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