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1579554 
Journal Article 
An improved synthesis of a beta-blocker celiprolol hydrochloride 
Ji, Li; Mao, XY; Qian, C; Chen, X 
2011 
1 
Journal of Chemical Research
ISSN: 1747-5198
EISSN: 2047-6507 
11 
640-643 
WOS:000298550000009 
Celiprolol hydrochloride, a beta-blocker drug, has been
synthesised from 4-chloronitrobenzene. The route involved hydrolysis of the chloride and
acetylation of the phenol, reduction of the nitro group, and acylation of theamine. This was
followed by Fries rearrangement of the acetyl group, Williamson etherification with
epichlorohydrin, followed by opening of the epoxide ring and salt formation. The overall yield of
celipropol was 39.1% on the basis of 4-chloronitrobenzene. The Fries rearrangement was
substantially improved. The process is suitable for industrial application because of its
convenient and environmentally friendly reaction conditions. 
celiprolol hydrochloride; 4-chloronitrobenzene; fries rearrangement; co-solvent; epichlorohydrin; beta-blockers