Formic Acid → 1,3-Benzoxazole-4-carboxylic acid

HRID 1870934Notes

Reaction equation

HRID 1870934 reaction equation
[NH2:1][C:2]1[C:10](N)=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH:12](O)=[O:13]>Cl>[O:13]1[C:10]2=[CH:9][CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]2[N:1]=[CH:12]1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 1980692,3-Diaminobenzoic acid

Product 1

HCID 183546021,3-Benzoxazole-4-carboxylic acidYield 77%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 2,3-diaminobenzoic acid (0.5 g, 3.29 mmol) and formic acid (405 μl, 9.87 mmol) in hydrochloric acid (4M, 10 ml) was heated under reflux for one hour. The precipitate which formed on cooling was collected, redissolved in boiling methanol, and decolorised with activated charcoal. Evaporation of the solvent gave benzoxazole-4-carboxylic acid as a white powder (407.9 mg, 77%)

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for one hour
  3. customThe precipitate which formed
  4. temperatureon cooling
  5. customwas collected
  6. dissolutionredissolved
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-a5a57b678a254af698fabb50223ce027
Source dataset
uspto-grants-2000_08
Patent number
US06100283

Reaction notes

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