GB1198752A - Substituted p-Chlorobenzoylanilines - Google Patents

Substituted p-Chlorobenzoylanilines

Info

Publication number
GB1198752A
GB1198752A GB1044768A GB1044768A GB1198752A GB 1198752 A GB1198752 A GB 1198752A GB 1044768 A GB1044768 A GB 1044768A GB 1044768 A GB1044768 A GB 1044768A GB 1198752 A GB1198752 A GB 1198752A
Authority
GB
United Kingdom
Prior art keywords
compound
acid
formula
group
general formula
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
GB1044768A
Inventor
John Martin Chemerda
Meyer Sletzinger
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.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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 Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB1198752A publication Critical patent/GB1198752A/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
    • C07D295/12—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 or doubly bound nitrogen atoms
    • C07D295/135—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 or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
    • C07C205/34—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups bound to carbon atoms of six-membered aromatic rings and etherified hydroxy groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—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
    • C07D209/26—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 with an acyl radical attached to the ring nitrogen atom
    • C07D209/28—1-(4-Chlorobenzoyl)-2-methyl-indolyl-3-acetic acid, substituted in position 5 by an oxygen or nitrogen atom; Esters thereof

Landscapes

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

Abstract

1,198,752. Indolylacetic acid derivatives. MERCK & CO Inc. 4 March, 1968 [9 March, 1967], No. 10447/68. Heading C2C. Indolylacetic acid derivatives of the general Formula (I) wherein R is a methoxy or dimethylamino group are prepared from substituted nitrophenylacetones via novel intermediates VIX as follows: 5-methoxy (or dimethylamino)- 2-nitro phenylacetone is reacted with a loweralkyl C 1-5 ortho-formate to form the corresponding ketal III, the nitro group of this being reduced to an amino group to yield a compound of general Formula (IV) where R is a lower alkyl C 1-5 group, N-acylating this with a p-chlorobenzoyl halide to obtain a compound of general Formula (V) and deketalizing this to form the corresponding phenylacetone VI; this is reacted with pyrrolidine in a solvent medium at reflux temperatures to form a compound of Formula (VII) which may be treated with an alkali metal salt of an α-haloacetic acid to obtain a compound of Formula (VIII) where X is an alkali metal atom and "hal" is a halogen atom, heating this in the presence of an aqueous acid whereby the desired indole derivative I is obtained as a precipitate in the reaction mixture and may be recovered therefrom; alternatively, the compound of Formula (VII) may be treated with a tetrahydropyranyl or a lower-alkyl ester C 1-5 of a haloacetic acid at reflux temperature to form a compound of Formula (IX) wherein R<SP>11</SP> is a tetrahydropyranyl or lower alkyl group C 1-5 , the carboxyl group is deesterified to yield the free acid X and this is refluxed in the presence of a strong acid to effect ring closure to form the corresponding indolylacetic acid I.
GB1044768A 1967-03-09 1968-03-04 Substituted p-Chlorobenzoylanilines Expired GB1198752A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CA984828 1967-03-09

Publications (1)

Publication Number Publication Date
GB1198752A true GB1198752A (en) 1970-07-15

Family

ID=4142839

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1044768A Expired GB1198752A (en) 1967-03-09 1968-03-04 Substituted p-Chlorobenzoylanilines

Country Status (5)

Country Link
CH (1) CH512468A (en)
DE (1) DE1668946A1 (en)
FR (1) FR1555404A (en)
GB (1) GB1198752A (en)
NL (1) NL6802550A (en)

Also Published As

Publication number Publication date
NL6802550A (en) 1968-09-10
CH512468A (en) 1971-09-15
FR1555404A (en) 1969-01-24
DE1668946A1 (en) 1971-09-30

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees