Sodium Hydroxide → 8-(2-Ethyl-6-methylbenzylamino)-3-hydroxymethyl-2-methylimidazo[1,2-a]pyridine-6-carboxylic acid

HRID 427480Notes

Reaction equation

HRID 427480 reaction equation
[CH2:1]([C:3]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[C:4]=1[CH2:5][NH:6][C:7]1[C:8]2[N:9]([C:16]([CH2:20][OH:21])=[C:17]([CH3:19])[N:18]=2)[CH:10]=[C:11]([C:13](N)=[O:14])[CH:12]=1)[CH3:2].[OH-:27].[Na+]>C(O)C>[CH2:1]([C:3]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[C:4]=1[CH2:5][NH:6][C:7]1[C:8]2[N:9]([C:16]([CH2:20][OH:21])=[C:17]([CH3:19])[N:18]=2)[CH:10]=[C:11]([C:13]([OH:27])=[O:14])[CH:12]=1)[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 97985998-(2-Ethyl-6-methylbenzylamino)-3-hydroxymethyl-2-methylimidazo(1,2-a)pyridine-6-carboxamide

Product 1

HCID 183574258-(2-Ethyl-6-methylbenzylamino)-3-hydroxymethyl-2-methylimidazo[1,2-a]pyridine-6-carboxylic acidYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8-(2-ethyl-6-methylbenzylamino)-3-hydroxymethyl-2-methylimidazo[1,2-a]pyridine-6-carboxamide (0.02 g, 0.057 m mol) and sodium hydroxide (0.02 g, 0.29 mmol) were solved in ethanol (95%) (1 ml) and was refluxed for 20 h. The solvent was evaporated under reduced pressure and to the residue was added water (1 ml). The pH was adjusted to 5 by addition of acetic acid and the solid that precipitated was isolated by filtration, washed with water and dried to give 0.012 g (60%) of the title compound.

Workup

  1. temperaturewas refluxed for 20 h
  2. customThe solvent was evaporated under reduced pressure and to the residue
  3. additionwas added water (1 ml)
  4. additionThe pH was adjusted to 5 by addition of acetic acid
  5. customthe solid that precipitated
  6. customwas isolated by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-6aa83b8cc2424a1b9b1eced0f9f3c9cb
Source dataset
uspto-grants-2001_11
Patent number
US06313136B1

Reaction notes

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