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GB1270413A - ESTERS OF alpha-1-AMINO-1,1-ALKYLIDENE MALONIC ACIDS - Google Patents

ESTERS OF alpha-1-AMINO-1,1-ALKYLIDENE MALONIC ACIDS

Info

Publication number
GB1270413A
GB1270413A GB9653/70A GB965370A GB1270413A GB 1270413 A GB1270413 A GB 1270413A GB 9653/70 A GB9653/70 A GB 9653/70A GB 965370 A GB965370 A GB 965370A GB 1270413 A GB1270413 A GB 1270413A
Authority
GB
United Kingdom
Prior art keywords
cyclopropylmethoxy
group
pyrocatechol
esters
alkylidene
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
GB9653/70A
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.)
Novartis AG
Original Assignee
Ciba Geigy 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 Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of GB1270413A publication Critical patent/GB1270413A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic 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
    • C07D215/16Heterocyclic 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
    • C07D215/20Oxygen atoms
    • C07D215/22Oxygen atoms attached in position 2 or 4
    • C07D215/233Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23KFODDER
    • A23K20/00Accessory food factors for animal feeding-stuffs
    • A23K20/10Organic substances
    • A23K20/116Heterocyclic compounds
    • A23K20/132Heterocyclic compounds containing only one nitrogen as hetero atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/44Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by —CHO groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00Ethers; Compounds having groups, groups or groups
    • C07C43/02Ethers
    • C07C43/20Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/205Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
    • C07C43/2055Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring containing more than one ether bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/008Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with tri- or tetrahalomethyl compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic 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
    • C07D215/16Heterocyclic 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
    • C07D215/48Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
    • C07D215/56Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Husbandry (AREA)
  • Zoology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Fodder In General (AREA)
  • Feed For Specific Animals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Physical Water Treatments (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Quinoline Compounds (AREA)

Abstract

1,270,413. Esters of α-(1-phenylamino-1,1- alkylidene) malonic acids. CIBA-GEIGY A.G. 16 June, 1969 [14 June, 1968; 24 Oct., 1968; 18 March, 1969], No. 9653/70. Divided out of 1,270,412. Addition to 1,205,639. Heading C2C. Novel alkylidene malonic acid esters of the formula in which Ph is a 1,2-phenylene residue substituted by a group -X 1 -A-R<SP>I</SP> and a group -X 2 -R<SP>II</SP> (in which RI is a cycloaliphatic radical, A is a direct bond or a bivalent aliphatic radical, each of X 1 and X 2 is oxygen or sulphur and R<SP>II</SP> is a C 8-20 aliphatic group), each of R 0 and R<SP>0</SP> 1 is carbo-C 1-7 -alkoxy, R 2 is hydrogen or C 1-7 alkyl and R 3 is hydrogen or an optionally substituted aliphatic or cycloaliphatic radical, or the tautomer of such a compound in which R 3 is hydrogen, are prepared by condensing an aniline containing the appropriate -X 1 -A-R<SP>I</SP> or -X 2 -R<SP>II</SP> substituents with a di-C 1-7 alkyl ester of an α-(1-C 1-7 alkoxy-1,1-alkylidene) malonic acid. Preferred compounds are dimethyl and diethyl esters of phenylaminomethylene-malonic acid in which the phenyl group is substituted by a cyclopropylmethoxy group and a decyloxy, dodecyloxy, octyloxy or tetradecyloxy group. The substituted aniline reactants are obtained by reduction of the co-responding nitro compounds. 4-Cyclopropylmethoxy - 3 - decyloxynitrobenzene is obtained by reacting cyclopropylmethyl bromide with pyrocatechol to yield pyrocatechol monocyclopropylmethyl ether which is condensed with benzoyl chloride to obtain 2- cyclopropylmethoxy-phenylbenzoate which is nitrated to 2 - cyclopropylmethoxy - 5 - nitrophenyl benzoate which on hydrolysis yields 4- ayclopropylmethoxy - 3 - hydroxy - nitrobenzene, reaction with decyl bromide providing the required ether. 3 - Cyclopropylmethoxy - 4- decyloxynitrobenzene is obtained by reacting pyrocatechol with decyl bromide, esterifying the resultant pyrocatechol monodecyl ether with benzoyl chloride to obtain 2-decyloxyphenyl benzoate which is nitrated, hydrolysing the 2- decyloxy - 5 - nitrophenyl benzoate obtained to 4 - decyloxy - 3 - hydroxy - nitrobenzene and reacting this with cyclopropylmethyl bromide to obtain the diether. 4-Cyclopropylmethoxy-3- dodecyloxy - nitrobenzene, 4 - cyclopropylmethoxy - 3 - octyloxynitrobenzene, and 2 - cyclopropylmethoxy-3-decyloxynitrobenzene are prepared by similar methods.
GB9653/70A 1968-06-14 1969-06-16 ESTERS OF alpha-1-AMINO-1,1-ALKYLIDENE MALONIC ACIDS Expired GB1270413A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US73696268A 1968-06-14 1968-06-14
US77042668A 1968-10-24 1968-10-24
US80833369A 1969-03-18 1969-03-18

Publications (1)

Publication Number Publication Date
GB1270413A true GB1270413A (en) 1972-04-12

Family

ID=27419219

Family Applications (2)

Application Number Title Priority Date Filing Date
GB9653/70A Expired GB1270413A (en) 1968-06-14 1969-06-16 ESTERS OF alpha-1-AMINO-1,1-ALKYLIDENE MALONIC ACIDS
GB30403/69A Expired GB1270412A (en) 1968-06-14 1969-06-16 3-quinoline-carboxylic acid compounds, process for their manufacture and compositions containing them

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB30403/69A Expired GB1270412A (en) 1968-06-14 1969-06-16 3-quinoline-carboxylic acid compounds, process for their manufacture and compositions containing them

Country Status (18)

Country Link
JP (1) JPS504673B1 (en)
AT (2) AT319725B (en)
BE (1) BE734566A (en)
CH (2) CH560193A5 (en)
DE (1) DE1929165A1 (en)
ES (1) ES368288A2 (en)
FI (1) FI49407C (en)
FR (1) FR2010879B1 (en)
GB (2) GB1270413A (en)
IE (1) IE33810B1 (en)
IL (1) IL32362A0 (en)
KE (2) KE2548A (en)
MY (2) MY7500154A (en)
NL (1) NL6908370A (en)
NO (2) NO132868C (en)
RO (1) RO56838A (en)
SE (2) SE387223B (en)
SU (1) SU561492A3 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0262305A1 (en) * 1986-08-29 1988-04-06 American Cyanamid Company Method for the preparation of anilinofumarate and quinoline-2,3-dicarboxylic acid

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU997646A1 (en) * 1978-11-27 1983-02-23 Ордена Трудового Красного Знамени Институт Органического Синтеза Ан Латвсср Fodder additive
JPS58219166A (en) * 1982-06-14 1983-12-20 Nippon Shinyaku Co Ltd 4-quinolone derivative
IL159320A0 (en) 2001-06-12 2004-06-01 Wellstat Therapeutics Corp Compounds for the treatment of metabolic disorders
AR099860A1 (en) * 2014-03-26 2016-08-24 Procter & Gamble PERFUME SYSTEMS

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0262305A1 (en) * 1986-08-29 1988-04-06 American Cyanamid Company Method for the preparation of anilinofumarate and quinoline-2,3-dicarboxylic acid
AU598023B2 (en) * 1986-08-29 1990-06-14 American Cyanamid Company Novel method for the preparation of quinoline-2, 3-dicarboxylic acid with anilinefumarates and dialkyloxalacetates

Also Published As

Publication number Publication date
FR2010879A1 (en) 1970-02-20
KE2547A (en) 1975-08-01
JPS504673B1 (en) 1975-02-22
AT319725B (en) 1975-01-10
MY7500154A (en) 1975-12-31
IE33810B1 (en) 1974-11-13
SE387223B (en) 1976-09-06
NL6908370A (en) 1969-12-16
GB1270412A (en) 1972-04-12
FI49407C (en) 1975-06-10
AT301547B (en) 1972-09-11
NO137072C (en) 1977-12-28
NO132868B (en) 1975-10-13
NO132868C (en) 1976-01-21
IE33810L (en) 1969-12-14
CH610732A5 (en) 1979-05-15
IL32362A0 (en) 1969-08-27
SE362424B (en) 1973-12-10
KE2548A (en) 1975-08-01
RO56838A (en) 1975-03-15
SU561492A3 (en) 1977-06-05
NO137072B (en) 1977-09-19
FR2010879B1 (en) 1976-09-03
DE1929165A1 (en) 1969-12-18
BE734566A (en) 1969-12-15
MY7500153A (en) 1975-12-31
FI49407B (en) 1975-02-28
CH560193A5 (en) 1975-03-27
ES368288A2 (en) 1971-05-01

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