GB760319A - Manufacture of basic ª -aryloxybutyric acid esters - Google Patents

Manufacture of basic ª -aryloxybutyric acid esters

Info

Publication number
GB760319A
GB760319A GB3628/53A GB362853A GB760319A GB 760319 A GB760319 A GB 760319A GB 3628/53 A GB3628/53 A GB 3628/53A GB 362853 A GB362853 A GB 362853A GB 760319 A GB760319 A GB 760319A
Authority
GB
United Kingdom
Prior art keywords
butyric acid
ester
phenoxy
phenyl
group
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
GB3628/53A
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.)
Hoechst AG
Original Assignee
Hoechst AG
Farbwerke Hoechst AG
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 Hoechst AG, Farbwerke Hoechst AG filed Critical Hoechst AG
Publication of GB760319A publication Critical patent/GB760319A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/20—Oxygen atoms
    • C07D215/24—Oxygen atoms attached in position 8
    • C07D215/26—Alcohols; Ethers thereof

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The invention comprises basic g -aryloxybutyric acid esters of the general formula <FORM:0760319/IV(b)/1> in which Ar represents a phenyl or naphthyl group or a phenyl nucleus fused on to a heterocyclic nucleus, or a halogen, alkyl, alkoxy or amino-substitution product of such a group or nucleus, and R1 and R2 each represent a methyl or ethyl group or together represent a divalent aliphatic radical forming a heterocyclic ring with the nitrogen atom, and water-soluble salts of such esters. Such compounds are obtained by esterifying the corresponding substituted butyric acid in the form of its acid chloride, or re-esterifying a lower (1-4 C) alkyl ester, especially the ethyl ester, of such acid, with an amino - alcohol of the formula HO.CH2 CH2.NR1R2, and converting the resulting ester into a water-soluble salt thereof. Radicals specified for "Ar" are methyl-phenyl, methylisopropyl-phenyl, o-, m- or p-halogenphenyl, a - or b -naphthyl, methoxyphenyl, o-, m- or p-aminophenyl, m-dimethylaminophenyl, and 8-quinolyl. The group -NR1R2 may be dimethyl- or diethylamino, piperidino, or hexamethylene-imino. In examples: (1) g -phenoxy-butyric acid chloride is reacted with (a) hexamethylen-imino-ethanol and (b) dimethylamino-ethanol, to form the corresponding esters; (2) g -(p-chlorophenoxy)-butyric acid ethyl ester and diethylaminoethanol are reacted in the presence of sodium to form g -(p-chlorophenoxy-butyric acid diethylaminoethylester. In a generally similar manner there are prepared (3) g -(b -naphthoxy)-butyric acid diethylor dimethylaminoethyl ester; (4) g -(2-isopropyl-5-methyl-phenoxy)-butyric acid diethylaminoethyl ester; (5) g -(a -naphthoxy)-butyric acid diethylaminoethyl ester; (6) g -(m-dimethylaminophenoxy)-butyric acid diethylaminoethyl ester; (7) g -(2-methoxy-phenoxy)-butyric acid diethylaminoethyl ester; (8) g -(8-quinolyl-oxy)-butyric acid diethylaminoethyl ester. Butyric acids. g -(m-Dimethylamino-phenoxy)-butyric acid is prepared by reacting m-dimethylaminophenol with g -butyrolactone. g - (8 - quinolyloxy) - butyric acid is prepared by reacting 8-oxy-quinoline with g -butyrolactone.
GB3628/53A 1952-02-07 1953-02-09 Manufacture of basic ª -aryloxybutyric acid esters Expired GB760319A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE760319X 1952-02-07

Publications (1)

Publication Number Publication Date
GB760319A true GB760319A (en) 1956-10-31

Family

ID=6661656

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3628/53A Expired GB760319A (en) 1952-02-07 1953-02-09 Manufacture of basic ª -aryloxybutyric acid esters

Country Status (1)

Country Link
GB (1) GB760319A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2120661A (en) * 1982-05-07 1983-12-07 Ciba Geigy Ag Quinoline derivatives and their use for the protection of cultivated plants
US4505738A (en) * 1982-05-10 1985-03-19 Ciba-Geigy Corporation Halovinyl-3,3-dimethylcyclopropanecarboxylic acid pyronyl esters useful for the protection of cultivated plants against the harmful effects of herbicides
US4749406A (en) * 1983-10-18 1988-06-07 Ciba-Geigy Corporation Quinoline derivatives and compositions thereof for the protection of cultivated plants

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2120661A (en) * 1982-05-07 1983-12-07 Ciba Geigy Ag Quinoline derivatives and their use for the protection of cultivated plants
US4505738A (en) * 1982-05-10 1985-03-19 Ciba-Geigy Corporation Halovinyl-3,3-dimethylcyclopropanecarboxylic acid pyronyl esters useful for the protection of cultivated plants against the harmful effects of herbicides
US4749406A (en) * 1983-10-18 1988-06-07 Ciba-Geigy Corporation Quinoline derivatives and compositions thereof for the protection of cultivated plants

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