Sodium Hydroxide → 2-Methyloxazolo[5,4-b]pyridine-5,6-dicarboxylic acid

HRID 742213Notes

Reaction equation

HRID 742213 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:9]([N:10]=1)=[CH:8][C:7]([C:11]([O:13]CC)=[O:12])=[C:6]([C:16]([O:18]CC)=[O:17])[N:5]=2.[OH-].[Na+]>CO.O>[CH3:1][C:2]1[O:3][C:4]2[C:9]([N:10]=1)=[CH:8][C:7]([C:11]([OH:13])=[O:12])=[C:6]([C:16]([OH:18])=[O:17])[N:5]=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19958238Diethyl 2-methyloxazolo[5,4-b]pyridine-5,6-dicarboxylate

Product 1

HCID 199581932-Methyloxazolo[5,4-b]pyridine-5,6-dicarboxylic acidYield 61%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of diethyl 2-methyloxazolo[5,4-b]pyridine-5,6-dicarboxylate (5.42 g, 0.0195 mol) dissolved in absolute methanol (160 mL) is added a 10% aqueous sodium hydroxide solution (36.1 mL, 0.0974 mol). A white precipitate slowly forms. The reaction is stirred at room temperature for one hour, diluted with water (20 mL) to dissolve the precipitate, and concentrated in vacuo. The residue is dissolved in water and acidified to pH 2-3 with concentrated HCl. The resulting white precipitate is collected by filtration, washed with water, and air dried to give 2-methyloxazolo[5,4-b]pyridine-5,6-dicarboxylic acid in 61% yield, melting point 235°-236° C. (dec).

Workup

  1. dissolutionto dissolve the precipitate
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue is dissolved in water
  4. filtrationThe resulting white precipitate is collected by filtration
  5. washwashed with water, and air
  6. customdried

Sources & evidence

ORD record
ord-8abe185ec5964214a90489fffbc0a422
Source dataset
uspto-grants-1996_09
Patent number
US05554579

Reaction notes

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