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

HRID 864304Notes

Reaction equation

HRID 864304 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-e57d2a29f0164ac0990d5ae4f3ca749b
Source dataset
uspto-grants-1996_10
Patent number
US05563113

Reaction notes

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