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Quinisocaine (
The Henry reaction between phthalaldehydic acid (2-Formylbenzoic acid) 19-67-5(1) and 1-nitropentane 28-05-7occurs by a mechanism that involves a hydroxy acid (2). Expulsion of water then gives (3). Reduction of the nitro group via catalytic hydrogenation leads to the amine
CID:158569430
(4). Treatment of that amine with sodium hydroxide leads to ring opening of the lactone ring to the intermediary amino acid (5). This cyclises spontaneously to the lactam so that the product isolated from the reaction mixture is in fact the isoquinoline derivative
CID:154188092
(7). Dehydration by means of strong acid gives 3-Butylisocarbostyril 32-90-1(8). Phosphorus oxychloride converts the oxygen function to the corresponding chloride via the enol forms 3-butyl-1-chloroisoquinoline 7-06-9(9). Displacement of halogen with the sodium salt from 2-dimethylaminoethanol (10) affords dimethisoquin (11).
INN
Inns are generally establishments or buildings where travelers can seek lodging, and usually, food and drink. Inns are typically located in the country or along a highway; before the advent of motorized transportation they also provided accommo ...
) or dimethisoquin (BAN
Ban, or BAN, may refer to:
Law
* Ban (law), a decree that prohibits something, sometimes a form of censorship, being denied from entering or using the place/item
** Imperial ban (''Reichsacht''), a form of outlawry in the medieval Holy Roman ...
and USAN) is a topical anesthetic A topical anesthetic is a local anesthetic that is used to numb the surface of a body part. They can be used to numb any area of the skin as well as the front of the eyeball, the inside of the nose, ear or throat, the anus and the genital area. Top ...
used as an antipruritic
Antipruritics, abirritants, or anti-itch drugs, are medications that inhibit the itching (Latin: ''pruritus'') often associated with sunburns, allergic reactions, eczema, psoriasis, chickenpox, fungal infections, insect bites and stings like those ...
.Synthesis
The Henry reaction between phthalaldehydic acid (2-Formylbenzoic acid) 19-67-5(1) and 1-nitropentane 28-05-7occurs by a mechanism that involves a hydroxy acid (2). Expulsion of water then gives (3). Reduction of the nitro group via catalytic hydrogenation leads to the amineCID:158569430
(4). Treatment of that amine with sodium hydroxide leads to ring opening of the lactone ring to the intermediary amino acid (5). This cyclises spontaneously to the lactam so that the product isolated from the reaction mixture is in fact the isoquinoline derivative
CID:154188092
(7). Dehydration by means of strong acid gives 3-Butylisocarbostyril 32-90-1(8). Phosphorus oxychloride converts the oxygen function to the corresponding chloride via the enol forms 3-butyl-1-chloroisoquinoline 7-06-9(9). Displacement of halogen with the sodium salt from 2-dimethylaminoethanol (10) affords dimethisoquin (11).
References
Local anesthetics Isoquinolines Phenol ethers Dimethylamino compounds {{dermatologic-drug-stub