2-Aminophenol → 2-Aminobenzoxazole

HRID 736432Notes

Reaction equation

HRID 736432 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(OCC)(=O)C.[N:15]#[C:16]Br.[OH-].[Na+]>O>[NH2:15][C:16]1[O:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=1

Participants

6

Reactant 4

HCID 58012-AminophenolHCID 8857Ethyl AcetateHCID 10476Cyanogen BromideHCID 14798Sodium Hydroxide

Product 1

HCID 207072-AminobenzoxazoleYield 88.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 2.5 g 2-aminophenol (6-1) and 20 ml ethyl acetate was heated to 45° C. 3 g of cyanogen bromide was added to the mixture. The mixture was stirred at 45-50° C. for 12 hours. After cooling to room temperature, 1.5 g of sodium hydroxide in 15 ml of water was added. The organic layer was separated and washed with brine until neutral pH. Toluene (5 ml) was added and the solvent was removed to yield 2.71 g (88%) 2-aminobenzoxazol (6-2).

Workup

  1. temperatureAfter cooling to room temperature
  2. customThe organic layer was separated
  3. washwashed with brine until neutral pH
  4. additionToluene (5 ml) was added
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-4fff7dbc93fc440fa233a24d4a547c75
Source dataset
uspto-grants-2009_09
Patent number
US07595334B2

Reaction notes

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