Epanolol is a

beta blocker Beta blockers, also spelled β-blockers, are a class of medications that are predominantly used to manage abnormal heart rhythms ( arrhythmia), and to protect the heart from a second heart attack after a first heart attack ( secondary prevention ...

. developed by

Imperial Chemical Industries Imperial Chemical Industries (ICI) was a British Chemical industry, chemical company. It was, for much of its history, the largest manufacturer in Britain. Its headquarters were at Millbank in London. ICI was listed on the London Stock Exchange ...

Synthesis

The

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

methyl 4-benzyloxyphenylacetate (1) is treated with

ethylenediamine Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately ...

to give the

amide In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a chemical compound, compound with the general formula , where R, R', and R″ represent any group, typically organyl functional group, groups or hydrogen at ...

(3). Separately, 2-cyanophenol (4) is reacted with

epichlorohydrin Epichlorohydrin (abbreviated ECH) is an organochlorine compound and an epoxide. Despite its name, it is not a halohydrin. It is a colorless liquid with a pungent, garlic-like odor, moderately soluble in water, but miscibility, miscible with most p ...

and

sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula . It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly corrosive base (chemistry), ...

to produce the

benzonitrile Benzonitrile is the chemical compound with the formula , abbreviated PhCN. This aromatic organic compound is a colorless liquid with a cherry or almond like odour. It is mainly used industrially to produce the melamine resin precursor benzoguanam ...

derivative (5). Combination of (3) and (5) by heating in

propanol There are two isomers of propanol. * 1-Propanol, ''n''-propanol, or propan-1-ol: CH3CH2CH2OH, the most common meaning *2-Propanol, isopropyl alcohol, isopropanol, or propan-2-ol: (CH3)2CHOH See also * Propanal (propionaldehyde) differs in spel ...

gives (6). Lastly, catalytic hydrogenation removes the benzyl

protecting group A protecting group or protective group is introduced into a molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction. It plays an important role in multistep organic synthesis. In man ...

and yields epanolol.

References

Beta blockers 4-Hydroxyphenyl compounds Benzamides Nitriles Phenoxypropanolamines {{antihypertensive-stub