GB760003A - A process for the production of alkamine esters of n-monoalkyl and n-monoalkoxyalkyl amino-hydroxybenzoic acids - Google Patents

A process for the production of alkamine esters of n-monoalkyl and n-monoalkoxyalkyl amino-hydroxybenzoic acids

Info

Publication number
GB760003A
GB760003A GB2343/52A GB234352A GB760003A GB 760003 A GB760003 A GB 760003A GB 2343/52 A GB2343/52 A GB 2343/52A GB 234352 A GB234352 A GB 234352A GB 760003 A GB760003 A GB 760003A
Authority
GB
United Kingdom
Prior art keywords
ester
amino
hydroxy
benzoic acid
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB2343/52A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rheinpreussen AG fuer Bergbau und Chemie
Original Assignee
Rheinpreussen AG fuer Bergbau und Chemie
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Rheinpreussen AG fuer Bergbau und Chemie filed Critical Rheinpreussen AG fuer Bergbau und Chemie
Publication of GB760003A publication Critical patent/GB760003A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/56—Nitrogen atoms
    • C07D211/58—Nitrogen atoms attached in position 4

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A process for the production of esters of N-monoalkyl- or N-monoalkoxyalkylaminohydroxybenzoic acids with amino-alcohols fully substituted at the nitrogen atom comprises alkylating or alkoxyalkylating the nuclear amino group of an alkamine ester of an aminohydroxybenzoic acid by a known method for the introduction of an alkyl group or an alkoxyalkyl group into an amino group. The alkylation or alkoxylation may be effected by reacting the alkamine ester with an alkyl halide or an alkoxyalkyl halide, and in the presence of an acid-binding agent, advantageously in an inert atmosphere and possibly under pressure. Alternatively the ester is condensed with a ketone, alkoxy-ketone, aldehyde or alkoxy-aldehyde and the condensation product obtained is hydrogenated to the N-monoalkyl or N-monoalkoxyalkyl derivative of the ester. The hydrogenation, which may be carried out simultaneously with the condensation, may be effected with hydrogen in the presence of Raney nickel or platinum dioxide. In examples: (1) 4-amino-2-hydroxy-benzoic acid diethylaminoethyl ester and n-butyl bromide are heated together to form the diethylaminoethyl ester of 4-n-butylamino-2-hydroxy-benzoic acid. Similarly prepared are (2) and (3), the corresponding 5-n-propylamino and 4-b -methoxyethylamino derivatives. In further examples: (4) the diethylaminoethyl ester of 4-amino-2-hydroxy-benzoic acid is condensed with propionaldehyde and the 4-propylideneamino-2-hydroxy-benzoic acid diethylaminoethyl ester obtained is hydrogenated to the diethylaminoethyl ester of 4-n-propylamino-2-hydroxybenzoic acid; (5) the dimethylaminoethyl ester of 4 - amino - 2 - hydroxy-benzoic acid and butyraldehyde in isopropanol are reacted while shaking the mixture with hydrogen in the presence of platinium oxide, to form the dimethylaminoethyl ester of 4-n-butylamino-2-hydroxy-benzoic acid. In a similar manner to (5) there are prepared (6) the piperidino-ethyl ester of 4-b -methoxyethylamino - 2 - hydroxybenzoic acid (and its hydrochloride and picrate); (7) and (8) the same compound as prepared in (1); (9) the same product as in (5). Specification 736,960 is referred to.
GB2343/52A 1951-02-07 1952-01-28 A process for the production of alkamine esters of n-monoalkyl and n-monoalkoxyalkyl amino-hydroxybenzoic acids Expired GB760003A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE760003X 1951-02-07

Publications (1)

Publication Number Publication Date
GB760003A true GB760003A (en) 1956-10-31

Family

ID=6660615

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2343/52A Expired GB760003A (en) 1951-02-07 1952-01-28 A process for the production of alkamine esters of n-monoalkyl and n-monoalkoxyalkyl amino-hydroxybenzoic acids

Country Status (1)

Country Link
GB (1) GB760003A (en)

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