Sodium Hydroxide → 2-Amino-5-(pyridin-4-yl)-1,3-thiazole-4-carboxylic acid

HRID 1906006Notes

Reaction equation

HRID 1906006 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[C:5]([C:7]([O:9]CC)=[O:8])[N:6]=1.[OH-].[Na+]>CO.O>[NH2:1][C:2]1[S:3][C:4]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[C:5]([C:7]([OH:9])=[O:8])[N:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 20145021Ethyl 2-amino-5-(pyridin-4-yl)-1,3-thiazole-4-carboxylate

Product 1

HCID 201449862-Amino-5-(pyridin-4-yl)-1,3-thiazole-4-carboxylic acidYield 79.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of ethyl 2-amino-5-(4-pyridyl)-4-thiazolecarboxylate (5.0 g) and sodium hydroxide (1.6 g) in a mixture of methanol (50 ml) and water (10 ml) was stirred at ambient temperature for an hour. The reaction mixture was evaporated in vacuo and the residue was dissolved in water. The aqueous solution was adjusted to pH 5 with 10% hydrochloric acid. The precipitate was collected by filtration and dried over phosphorus pentoxide in vacuo to afford 2-amino-5-(4-pyridyl)-4-thiazolecarboxylic acid (3.54 g).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. dissolutionthe residue was dissolved in water
  3. filtrationThe precipitate was collected by filtration
  4. dry with materialdried over phosphorus pentoxide in vacuo

Sources & evidence

ORD record
ord-e48138b7789b4b7e92f7b034976d697b
Source dataset
uspto-grants-1987_03
Patent number
US04649146

Reaction notes

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