ChemicalBook CAS DataBase List ethyl 2-(4-aminophenyl)propionate

ethyl 2-(4-aminophenyl)propionate synthesis

10synthesis methods

Product Name:ethyl 2-(4-aminophenyl)propionate
CAS Number:32868-25-0
Molecular formula:C11H15NO2
Molecular Weight:193.24

64-17-5 Synthesis

64-17-5
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19910-33-9
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32868-25-0
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Yield:32868-25-0 74%

Reaction Conditions:

Stage #1: ethanol;2-(4-nitrophenyl)propanoic acidwith thionyl chloride at 50 - 65; for 2 h;Large scale;
Stage #2: with iron(III) chloride;hydrazine hydrate;water;sodium hydrogencarbonate;pyrographite at 25 - 80; pH=6.5 - 7.5; for 1 h;Large scale;

Steps:

1.2 (2) Synthetic AMLF04

AMLF02 (100kg) was added to the reaction flask, absolute ethanol (400L) was added, the temperature was raised to 50-55°C, and thionyl chloride (42.6kg) was added dropwise.After dripping, the reaction is kept at 60~65°C for 2h, and the reaction is over.Cool down to 25-30°C, adjust the pH to 6.5-7.5 with sodium bicarbonate aqueous sodium solution. Add the pre-prepared catalyst (230kg) (water 2vol. + ferric chloride 0.07eq. + activated carbon 4eq. + sodium bicarbonate 0.07eq.),Turn on the stirring and heat to 70-80°C (start dripping at 75°C), add hydrazine hydrate (1.8eq.) dropwise, keep the temperature and react for 1h. The reaction is over. Cool down to 20-30°C, add diatomaceous earth to the reaction kettle and stir for 1h, filter, and neutralize the filtrate to 7-8 with concentrated hydrochloric acid.Concentrate under reduced pressure to remove ethanol, add toluene (640kg) to extract the remaining aqueous phase twice, filter through silica gel, and concentrate the filtrate under reduced pressure at 60-65°C to obtain 79.1kg of AMLF04 with a purity of 98.5%. The total yield of the two steps is 74%.The entire reaction described above takes about 50 hours.

References:

CN113135831,2021,A Location in patent:Paragraph 0048; 0052-0054

67-56-1 Synthesis