Sulfuric Acid → Oxazolo[4,5-b]pyridin-2-yl(phenyl)methanone

HRID 66352Notes

Reaction equation

HRID 66352 reaction equation
[CH2:1]([C:8]1[O:9][C:10]2[C:11]([N:16]=1)=[N:12][CH:13]=[CH:14][CH:15]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mn]([O-])(=O)(=O)=[O:18].[K+].S(=O)(=O)(O)O.S(=O)(O)[O-].[Na+]>[OH-].[Na+].O>[C:1]([C:8]1[O:9][C:10]2[C:11]([N:16]=1)=[N:12][CH:13]=[CH:14][CH:15]=2)(=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 516875Potassium PermanganateHCID 227548052-Benzyloxazolo[4,5-b]pyridineHCID 23665763Sodium Bisulfite

Product 1

HCID 22754809Oxazolo[4,5-b]pyridin-2-yl(phenyl)methanone

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 962WaterSolvent

Procedure

A mixture of 800 mg. of 2-benzyloxazolo[4,5-b]pyridine, 2.5 g. of potassium permanganate, 35 ml. of water and 6 drops of 2.5 N sodium hydroxide solution was heated at 50°-55° C. for 3 hours. After cooling, sulfuric acid was added to about pH 6 and sufficient sodium bisulfite was added to remove the manganese dioxide. The crystalline precipitate remaining was collected and recrystallized from ethylacetate to give 2-benzoyloxazolo[4,5-b]pyridine, m.p. 151°-153° C.

Workup

  1. additionA mixture of 800 mg
  2. temperatureAfter cooling
  3. additionwas added
  4. customto remove the manganese dioxide
  5. customThe crystalline precipitate remaining was collected
  6. customrecrystallized from ethylacetate

Sources & evidence

ORD record
ord-c32ca1f760c7496791ecdcdf0b8c4ce7
Source dataset
uspto-grants-1978_12
Patent number
US04131677

Reaction notes

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