2-Amino-4-methylphenol → 5-Methyl-benzooxazole-2-carboxylic acid ethyl ester

HRID 29440

Reaction equation

HRID 29440 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[OH:9].[CH2:10]([O:12][C:13](OCC)([O:19]CC)[C:14](OCC)=O)[CH3:11]>>[CH2:10]([O:12][C:13]([C:14]1[O:9][C:3]2[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[N:1]=1)=[O:19])[CH3:11]

Participants

3

Reactant 2

HCID 72642-Amino-4-methylphenolHCID 5090273Ethyl 2,2,2-triethoxyacetate

Product 1

HCID 687130605-Methyl-benzooxazole-2-carboxylic acid ethyl esterYield 91%

Conditions

Temperature
110 °C

Procedure

To 2-amino-4-methylphenol (1 g, 8.1 mmol) was added ethyl triethoxyacetate (5.4 g, 3 eq). The mixture was stirred at 110° C. overnight. The reaction mixture was cooled and triturated with hexane. Filtration gave 850 mg (91%) of 5-methyl-benzooxazole-2-carboxylic acid ethyl ester as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customtriturated with hexane
  3. filtrationFiltration

Sources & evidence

ORD record
ord-8b7b0d44b47645e18d89b4e26aef221a
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Linked notes

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