Anthranilic Acid → ortho-aminophenylbenzoxazole

HRID 1006391Notes

Reaction equation

HRID 1006391 reaction equation
[C:1]([OH:10])(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1O>>[NH2:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]1[O:10][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=1

Participants

3

Reactant 2

HCID 227Anthranilic AcidHCID 58012-Aminophenol

Product 1

HCID 4602658ortho-aminophenylbenzoxazoleYield 49%

Procedure

The reaction of 13.71 g (0.10 mole) of anthranilic acid with 10.91 g (0.10 mole) of ortho-aminophenol was carried out in 100 ml of polyphosphoric acid at 200° C. After 10 hours from the start of the reaction, the reaction mixture was poured into ice water and the precipitate was filtered and dried. The solid thus obtained was purified by column chromatography and concentrated to give 10.28 g (0.048 mole, 49%) of ortho-aminophenylbenzoxazole.

Workup

  1. customAfter 10 hours from the start of the reaction
  2. filtrationthe precipitate was filtered
  3. customdried
  4. customThe solid thus obtained
  5. customwas purified by column chromatography
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3186a28d983d441fbe66548a3c4dcfec
Source dataset
uspto-grants-2004_09
Patent number
US06790540B2

Reaction notes

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