2-Aminophenol → Benzoxazole, 2-(4-pyridyl)-

HRID 1636852Notes

Reaction equation

HRID 1636852 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[O:8])=[CH:3][CH:2]=1.[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1O>C(O)(=O)C>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[O:8][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=2)=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 58012-AminophenolHCID 133894-Pyridinecarboxaldehyde

Product 1

HCID 16804Benzoxazole, 2-(4-pyridyl)-

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A 500 mg portion of pyridine-4-aldehyde was dissolved in 15 ml of acetic acid, and the solution was mixed with 509 mg of o-aminophenol and stirred with heating at 100° C. for 6 hours. The solvent was concentrated under a reduced pressure, and the residual oily matter was mixed with saturated sodium bicarbonate aqueous solution and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with magnesium sulfate, and then the solvent was evaporated under a reduced pressure. Thereafter, the thus obtained mixture was purified by a silica gel column chromatography (ethyl acetate:hexane=1:1) to obtain the title compound (90 mg) in light yellow color.

Workup

  1. concentrationThe solvent was concentrated under a reduced pressure
  2. additionthe residual oily matter was mixed with saturated sodium bicarbonate aqueous solution
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. customthe solvent was evaporated under a reduced pressure
  7. customThereafter, the thus obtained mixture was purified by a silica gel column chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-cb40c3c5630e49eb885b82d69c249c65
Source dataset
uspto-grants-2000_03
Patent number
US06037342

Reaction notes

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