GB377464A - Manufacture of substituted aromatic ketones - Google Patents

Manufacture of substituted aromatic ketones

Info

Publication number
GB377464A
GB377464A GB23745/31A GB2374531A GB377464A GB 377464 A GB377464 A GB 377464A GB 23745/31 A GB23745/31 A GB 23745/31A GB 2374531 A GB2374531 A GB 2374531A GB 377464 A GB377464 A GB 377464A
Authority
GB
United Kingdom
Prior art keywords
methoxyacetophenone
oxy
interaction
prepared
diethylaminoethoxy
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
GB23745/31A
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.)
BASF Schweiz AG
Original Assignee
Gesellschaft fuer Chemische Industrie in Basel CIBA
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 Gesellschaft fuer Chemische Industrie in Basel CIBA filed Critical Gesellschaft fuer Chemische Industrie in Basel CIBA
Publication of GB377464A publication Critical patent/GB377464A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups

Landscapes

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

Abstract

Aminoalkoxy derivatives of aromatic ketones are prepared by introducing an aminoalkyl residue, the tertiary amino group of which is substituted by alkyl, aralkyl or cycloalkyl, into an hydroxyl group of an aromatic ketone containing nuclear hydroxyl. The products are useful therapeutically. According to the examples, (1) p-diethylaminoethoxyacetophenone is obtained by treating p-oxyacetophenone with chlorethyldiethylamine or by interaction of p-bromethoxyacetophenone (obtained, together with a little di-p-acetophenylglycolether, by interaction of p-oxyacetophenone with ethylene bromide) with diethylamine; (2) 2-diethylaminoethoxy-4-methoxyacetophenone is prepared by heating 2-oxy-4-methoxyacetophenone with bromoethyldiethylamine hydrobromide in the presence of potash; (3) (2-di-ethylaminoethoxy-4-methoxyphenyl)-benzyl-ketone results from the interaction of (2-oxy-4-methoxyphenyl)-benzylketone with chlorethyldiethylamine; (4) treatment of p-oxybenzophenone with chlorethyldicyclohexylamine gives p-dicyclohexylaminoethoxybenzophenone; (5) 2-oxy-4-methoxyacetophenone is heated with ethylene bromide in the presence of sodium alcoholate and the resulting 2-bromethoxy-4-methoxyacetophenone boiled with methylbenzylamine hydrobromide in benzene solution to form 2-methylbenzylaminoethoxy-4-methoxyacetophenone; (6) 2-oxyethoxy-4-methoxyacetophenone is first prepared by treating p 2-oxy-4-methoxyacetophenone with excess of ethylene oxide, then heated with phosphorus pentachloride, and the 2-chlorethoxy-4-methoxyacetophenone so obtained heated with diethylamine to give the 2-diethylaminoethoxy compound; (7) 2-diethylaminoisobutyloxy-4-methoxyacetophenone is obtained by heating 2-oxy-4-methoxyacetophenone with 1-diethyl-amino-3-chloro-n-butane in the presence of sodium alcoholate. The following compounds are prepared in an analogous manner:--m-diethylaminoethoxyacetophenone, 2 - diethyl-aminoethoxy - 4 - methoxy - 5 - nitroacetophenone (which may be reduced to the 5-amino compound and this then acetylated) from 2-oxy-4-methoxy-5-nitroacetophenone, 2-diethylaminoethoxy-4-n-butyloxyacetophenone from 2-oxy-4-n-butyloxyacetophenone (obtainable by interaction of the monosodium salt of 1-acetyl-2 : 4-dioxybenzene with n-butyl bromide), 2-diethylaminoethoxy-4-benzyloxyacetophenone from 2-oxy-4-benzyloxyacetophenone (prepared by treatment of the monosodium salt of 1-acetyl-2 : 4-dioxybenzene with benzyl chloride), 1-di-ethylaminoethoxy-2-acetylnaphthalene, 2-di-ethylaminoethoxy - 4 - methoxybutyrophenone from 2-oxy-4-methoxybutyrophenone (obtained from the monosodium salt of 2 : 4-dioxybutyrophenone and dimethyl sulphate), p-diethylaminoethoxyphenylbenzylketone, (2-diethylaminoethoxy-4-benzyloxyphenyl)-benzylketone from (2-oxy-4-benzyloxyphenyl)-benzylketone (obtainable by interaction of the monosodium salt of 2 : 4-dioxyphenylbenzylketone with benzyl chloride), and 2-di-n-butylaminoethoxy-4-methoxyacetophenone. The Specification as open to inspection under Sect. 91 (3) (a) describes also the aminoalkylation of aromatic aldehydes containing nuclear hydroxyl and includes an example of the preparation of o-diethylaminoethoxybenzaldehyde by interaction of salicylaldehyde with the p-toluenesulphonic ester of diethylaminoethanol. This subject-matter does not appear in the Specification as accepted. 1-Diethylamino-3-chloro-n-butane is prepared by boiling b -diethylaminoethylmethylcarbinol (obtained by reduction of b -diethylaminoethylmethylketone) with thionyl chloride.
GB23745/31A 1930-08-28 1931-08-24 Manufacture of substituted aromatic ketones Expired GB377464A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH377464X 1930-08-28

Publications (1)

Publication Number Publication Date
GB377464A true GB377464A (en) 1932-07-28

Family

ID=4513601

Family Applications (1)

Application Number Title Priority Date Filing Date
GB23745/31A Expired GB377464A (en) 1930-08-28 1931-08-24 Manufacture of substituted aromatic ketones

Country Status (1)

Country Link
GB (1) GB377464A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3235598A (en) * 1963-03-14 1966-02-15 Upjohn Co Aminoalkoxy-substituted-salicylaldehydes
GB2154587A (en) * 1981-12-24 1985-09-11 Delalande Sa Aminoalkoxy-substituted aromatic ketones

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3235598A (en) * 1963-03-14 1966-02-15 Upjohn Co Aminoalkoxy-substituted-salicylaldehydes
GB2154587A (en) * 1981-12-24 1985-09-11 Delalande Sa Aminoalkoxy-substituted aromatic ketones

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