Picolinic acid → Benzoxazole, 2-(2-pyridinyl)-

HRID 1287667Notes

Reaction equation

HRID 1287667 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15](O)=O.[OH-].[Na+]>O>[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[O:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 1018Picolinic acidHCID 58012-AminophenolHCID 14798Sodium Hydroxide

Product 1

HCID 135005Benzoxazole, 2-(2-pyridinyl)-Yield 78.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
210 °C

Procedure

A mixture of o-aminophenol (10.9 g, 0.1 mole), picolinic acid (12.3 g, 0.1 mole) and polyphosphoric acid (275 g) is heated under a nitrogen atmosphere at 210° C for 3 hours. The mixture is then cooled to 160° C and slowly poured into 1 liter of water. The mixture is neutralized with 50% sodium hydroxide solution yielding 15.4 g of the title compound as a crystalline solid, melting point 105°-107° C.

Workup

  1. temperatureThe mixture is then cooled to 160° C

Sources & evidence

ORD record
ord-44bfc3c52329438ea9e535c11eae7467
Source dataset
uspto-grants-1976_10
Patent number
US03985755

Reaction notes

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