Reaktion #565307

Reaktionsgleichung

ethyl acetate

acetic acid

acetic acid

HCl

2-methyl-N-(4-nitro phenyl) acrylamide

→

N-(4-amino phenyl)-2-methyl acrylamide hydrochloride

Ausbeute 72.7%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed
2. 2
   workup.ADDITIONwas added
3. 3
   TemperaturA proper cooling
4. 4
   Sonstigea safe gas separation
5. 5
   SonstigeDuring the first reaction step a very strong exothermic gas release
6. 6
   Temperaturwhile refluxing
7. 7
   Filtrationthe Fe salts were suction-filtered
8. 8
   WaschenThe salts were then washed with 1.9 L of ethyl acetate
9. 9
   workup.STIRRINGWhile stirring
10. 10
    workup.STIRRINGwhile stirring
11. 11
    FiltrationThe precipitate was suction-filtered
12. 12
    Waschenwashed with ethyl acetate
13. 13
    SonstigeAfter drying at 40° C

Vorschrift

A mixture of 114 g of 2-methyl-N-(4-nitro phenyl) acrylamide (=0.55 mol) and 92.6 g of Fe powder (=1.65 mol=3 mol equiv.) in 420 ml of ethanol was refluxed. Upon refluxing 400 ml of acetic acid (=6.6 mol=12 mol equiv.) was added. A proper cooling and a safe gas separation were ensured. During the first reaction step a very strong exothermic gas release occurred. After completing of the addition of acetic acid, stirring while refluxing was continued for 60 min. After TLC inspection 300 ml of ethyl acetate was added and the Fe salts were suction-filtered. The salts were then washed with 1.9 L of ethyl acetate. While stirring, 138 ml of HCl conc. (1.65 mol=3 equiv.) was added to the filtrate. The mixture was cooled to 5° C. while stirring. The precipitate was suction-filtered and washed with ethyl acetate. After drying at 40° C. 85 g of N-(4-amino phenyl)-2-methyl acrylamide hydrochloride was obtained (i.e. 72% versus 117 g theor.)

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