Reaction #81522

Reaction equation

2-amino-5-methoxybenzoic acid, methyl ester

Sodium hydride

acetamide oxime

→

title compound

Yield 72.4%

4-Methoxy-2-(3-methyl-1,2,4-oxadiazol-5-yl)benzenamine

Yield 72.4%

Solvents

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   TemperatureThe mixture was heated at 60° for 30 min
2. 2
   Temperatureat reflux for 2.5 h
3. 3
   Temperatureto cool
4. 4
   Filtrationfiltered
5. 5
   Otherthe filtrate evaporated

Procedure

Sodium hydride (594 mg) was added to a stirred suspension of acetamide oxime (1.0 g) and 4 molecular sieves (4 g) in dry tetrahydrofuran (50 ml) under nitrogen. The mixture was heated at 60° for 30 min then allowed to cool to room temperature. A solution of 2-amino-5-methoxybenzoic acid, methyl ester (2.0 g) in dry tetrahydrofuran (20 ml) was added and the mixture stirred at reflux for 2.5 h. The suspension was allowed to cool, filtered and the filtrate evaporated to give the title compound as a yellow solid (1.64 g)

Source