3-Hydroxyanthranilic Acid → 2-Phenylbenzoxazole-4-carboxylic acid

HRID 415234Notes

Reaction equation

HRID 415234 reaction equation
[C:1](O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:13]([C:14]([OH:16])=[O:15])[C:12]=1[NH2:20]>O>[C:2]1([C:1]2[O:10][C:11]3[C:12](=[C:13]([C:14]([OH:16])=[O:15])[CH:17]=[CH:18][CH:19]=3)[N:20]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 863-Hydroxyanthranilic AcidHCID 243Benzoic Acid

Product 1

HCID 108683692-Phenylbenzoxazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

Benzoic acid (122 mg, 1.0 mmol) and 3-hydroxyanthranilic acid (153 mg, 1.0 mmol) were added to PPA (1 g), the mixture was stirred at 180° C. for 2 hr. After cooled to room temperature, water (50 mL) was added and filtered; the cake was washed with water and dried in vacuum to obtain 2-phenylbenzo[d]oxazole-4-carboxylic acid. LC-MS (ESI) m/z 240 [M+1]+.

Workup

  1. temperatureAfter cooled to room temperature
  2. filtrationfiltered
  3. washthe cake was washed with water
  4. customdried in vacuum

Sources & evidence

ORD record
ord-222ea400035044a09efbc7739839e895
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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