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

HRID 1457823Notes

Reaction equation

HRID 1457823 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[C:9](O)(=O)[C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1.B(O)(O)O>C1(C)C(C)=CC=CC=1>[O:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:9]1[C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 58012-AminophenolHCID 5922Isonicotinic AcidHCID 7628Boric Acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 2-aminophenol (10.9 g, 100 mmol), isonicotinic acid (12.3 g, 100 mmol) and boric acid (6.1 g, 100 mmol) in xylene (500 ml) was heated at reflux, under a nitrogen atmosphere, for 17 hours. The mixture was cooled to room temperature and the orange suspension partitioned between sodium hydroxide solution (4N, 500 ml) and ethyl acetate (500 ml), the phases were separated and the organic layer washed with sodium hydroxide solution (2N, 2×300 ml), water (100 ml) and brine (100 ml).

Workup

  1. temperaturewas heated
  2. temperatureat reflux, under a nitrogen atmosphere, for 17 hours
  3. customthe orange suspension partitioned between sodium hydroxide solution (4N, 500 ml) and ethyl acetate (500 ml)
  4. customthe phases were separated
  5. washthe organic layer washed with sodium hydroxide solution (2N, 2×300 ml), water (100 ml) and brine (100 ml)

Sources & evidence

ORD record
ord-29925d1218744236b8aa0930c1edee37
Source dataset
uspto-grants-1998_12
Patent number
US05849765

Reaction notes

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