Reaction #566766

Reaction equation

2,5-dimethoxyaniline

formylphenylacetate

toluene

toluene

HCl

→

compound 10

Yield 72.0%

Ethyl (Z)-3-(2,5-dimethoxyanilino)-2-phenyl-2-propenoate

Yield 72.0%

Conditions

Workup

1. 1
   TemperatureAfter cooling
2. 2
   ExtractionAfter extraction
3. 3
   Otherthe organic phase obtained
4. 4
   Dryingis dried over MgSO4
5. 5
   Otherevaporated under reduced pressure
6. 6
   OtherThe isolated residue is crystallized from methanol
7. 7
   Filtrationfiltered through a sinter funnel

Procedure

A solution of 2,5-dimethoxyaniline (1.76 g, 11.49 mmol) and ethyl ∀-formylphenylacetate (2.43 g, 1.1 eq) in toluene (20 ml) is refluxed for 18 hours. After cooling, the reaction mixture is diluted with toluene (10 ml) and then acidified with 10% HCl. After extraction, the organic phase obtained is dried over MgSO4 and then evaporated under reduced pressure. The isolated residue is crystallized from methanol and then filtered through a sinter funnel to give 2.71 g (72%) of compound 10.

Source