ChemicalBook CAS DataBase List 3-[(4-chlorophenyl)amino]propanoic acid

3-[(4-chlorophenyl)amino]propanoic acid synthesis

5synthesis methods

Product Name:3-[(4-chlorophenyl)amino]propanoic acid
CAS Number:21617-19-6
Molecular formula:C9H10ClNO2
Molecular Weight:199.63

106-47-8 Synthesis

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79-10-7 Synthesis

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21617-19-6
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Yield:21617-19-6 87%

Reaction Conditions:

with sodium hydroxide;sodium chloride in water monomer;

Steps:

264.1 [Step 1]

[Step 1] Synthesis of N-(4-chlorophenyl)-β-alanine p-chloroaniline (200 g) was suspended in water (100 ml) and acrylic acid (54.1 ml) was added to the suspension. The mixture was heated under reflux for 2 hours in a nitrogen atmosphere. After allowing to cool, 2 N aqueous solution of sodium hydroxide (500 ml) was added, and the mixture was extracted with ether. The aqueous layer was adjusted to pH 3 with 1 N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The title compound (137.3g, 87%) was obtained without further purification. m.p.: 119.0-12 1.0° C. IR spectrum (KBr tab.) νcm^-1: 1707, 1599, 1508, 1435, 1329, 1219, 816. NMR spectrum (*DMSO-d₆) δ ppm: 7.08 (2H, d, J=8.9 Hz), 6.56 (2H, d, J=8.9 Hz), 5.83 (1H, bs), 3.21 (2H, t, J=6.8 Hz), 2.50-2.45 (2H, m).

References:

US6018046,2000,A