Sodium Hydroxide → 2,3-Dimethyl-8-(2-ethyl-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylic acid

HRID 427501Notes

Reaction equation

HRID 427501 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([NH:10][CH2:11][C:12]3[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:19][CH3:20])=[CH:8][C:7]([C:21]([O:23]C)=[O:22])=[CH:6][N:5]2[C:25]=1[CH3:26].[OH-].[Na+]>O1CCOCC1>[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([NH:10][CH2:11][C:12]3[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:19][CH3:20])=[CH:8][C:7]([C:21]([OH:23])=[O:22])=[CH:6][N:5]2[C:25]=1[CH3:26]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18357442Methyl 2,3-dimethyl-8-(2-ethyl-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylate

Product 1

HCID 118239362,3-Dimethyl-8-(2-ethyl-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylic acidYield 94.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl 2,3-dimethyl-8-(2-ethyl-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylate (0.4 g, 1.1 mmol) was added to a mixture of 1,4-dioxane (6 ml) and 2 M NaOH (6 ml) and was refluxed for 30 min. The dioxane was evaporated under reduced pressure and the aqueous solution was made acidic by addition of 2 M HCl. The acidic aqueous was basified by the addition of a saturated bicarbonate solution and the solid that formed was isolated by filtration to give 0.35 g (91%) of the title compound.

Workup

  1. temperaturewas refluxed for 30 min
  2. customThe dioxane was evaporated under reduced pressure
  3. additionthe aqueous solution was made acidic by addition of 2 M HCl
  4. additionThe acidic aqueous was basified by the addition of a saturated bicarbonate solution
  5. customthe solid that formed
  6. customwas isolated by filtration

Sources & evidence

ORD record
ord-ea836ea6b0494f6c9058173f752e4854
Source dataset
uspto-grants-2001_11
Patent number
US06313137B1

Reaction notes

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