Réaction #170994

Équation de réaction

(4-Nitrophenoxy)-acetic acid methoxycarbonyl methyl ester

(4-Nitrophenoxy)-acetic acid methoxycarbonylmethyl ester

→

45

Rendement 73.1%

(4-Aminophenoxy)-acetic acid methoxycarbonylmethyl ester

Rendement 73.1%

Solvants

dimethyl formamide

Conditions de réaction

Traitement

1. 1
   AutreThe catalyst was removed by filtration and ice water (400 ml)
2. 2
   workup.ADDITIONwas added to the filtrate
3. 3
   ExtractionCrude 45 was extracted into ethyl acetate
4. 4
   Séchagedried over Na2SO4
5. 5
   workup.DISTILLATIONdistilled
6. 6
   AutreCrude 45 was then recrystallised from chloroform:hexane (1:6)

Mode opératoire

(4-Nitrophenoxy)-acetic acid methoxycarbonyl methyl ester 44 (20 g, 74.3 mmol) was dissolved in dimethyl formamide (100 ml) in a pressure vessel. Palladium on carbon (5%, 8 g) was added, and the mixture stirred under an atmosphere of hydrogen (4 kg) for 2 hours. The catalyst was removed by filtration and ice water (400 ml) was added to the filtrate. Crude 45 was extracted into ethyl acetate, dried over Na2SO4 and distilled. Crude 45 was then recrystallised from chloroform:hexane (1:6) to get pure 45 (13 g, 73%) as a light brown shining powder with an m.p. between 76.5-78.5° C.

Source