4-amino-5-chloro-2,3-dihydrobenzofuran-7-carboxylic acid Chemical Properties

Melting point:

242 °C(dec.)

Boiling point:

406.5±45.0 °C(Predicted)

Density 

1.566

storage temp. 

2-8°C(protect from light)

solubility 

DMSO (Slightly), Methanol (Slightly, Heated)

form 

Solid

pka

4.45±0.20(Predicted)

color 

Light Brown

InChI

InChI=1S/C9H8ClNO3/c10-6-3-5(9(12)13)8-4(7(6)11)1-2-14-8/h3H,1-2,11H2,(H,12,13)

InChIKey

KRMUVKSAOVLXLF-UHFFFAOYSA-N

SMILES

O1C2=C(C(O)=O)C=C(Cl)C(N)=C2CC1

Safety Information

HS Code 

2932990090

4-amino-5-chloro-2,3-dihydrobenzofuran-7-carboxylic acid Usage And Synthesis

Uses

4-Amino-5-chloro-2,3-dihydro-7-benzofurancarboxylic Acid, can be used as an intermediate for the synthesis of Prucalopride (P838950), a selective 5-HT4 receptor agonist used effective for chronic constipation.

Synthesis

Firstly, adding methyl 4-(acetyl amino)-2-hydroxy-3-(2-hydroxy ethyl) benzoate into an organic solvent, adding triphenylphosphine and azo dioctyl phthalate diethyl ester, performing cyclization to obtain a methyl 4-acetamido-2,3-dihydro benzofuran-7-formate rough product, directly chloridizing the rough product by using N-chloro succinimide to obtain a rough product methyl 4-acetamide amino-5-chloro-7-benzofuran formate, and performing hydrolysis and purification to obtain a 4-amino-5-chloro-2,3-dihydrobenzofuran-7-carboxylic acid pure product.