GB459453A - Process for the manufacture of condensation products containing nitrogen - Google Patents

Process for the manufacture of condensation products containing nitrogen

Info

Publication number
GB459453A
GB459453A GB1936535A GB1936535A GB459453A GB 459453 A GB459453 A GB 459453A GB 1936535 A GB1936535 A GB 1936535A GB 1936535 A GB1936535 A GB 1936535A GB 459453 A GB459453 A GB 459453A
Authority
GB
United Kingdom
Prior art keywords
methoxy
amino
quinoline
butyrolactone
acetobutyrolactone
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
GB1936535A
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie 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
Priority to DEI52656D priority Critical patent/DE663375C/en
Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to GB1936535A priority patent/GB459453A/en
Publication of GB459453A publication Critical patent/GB459453A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Butyrolactones containing a keto group attached to the carbon atom in a -position to the carbonyl group are condensed with primary amines of the aromatic or heterocyclic series to give products of the type <FORM:0459453/IV/1> wherein R stands for a hydrocarbon radicle, R1 for the butyrolactone radicle which may be substituted, and R2 for an aromatic or heterocyclic radicle. Suitable butyrolactones are a -aceto- and a -benzoyl-butyrolactone and their alkyl or hydroxyalkyl substitution products, whilst as bases may be employed aniline and its nuclear substitution products, aminopyridines, aminoquinolines and aminoalkylamino compounds of the aromatic and heterocyclic series. When heated with dilute mineral acid, the products decompose to 1 mol of the original amine, 1 mol of carbon dioxide and 1 mol of a keto-alcohol. Examples describe the condensation of (1) a -acetobutyrolactone with aniline, m-chloraniline, p-anisidine, o-toluidine, p-phene,tidine, p - aminophenol - b - diethylaminoethylether, p-diethylamino-aniline and p-aminoacetanilide; (2) a -acetobutyrolactone with 2 : 6-diaminopyridine, 1-phenyl-2 : 3-dimethyl-4-amino-5-pyrazolone, 6-methoxy-8-aminoquinoline, 6-amino-8-b -diethylaminoethoxyquinoline, 2-methoxy-6-chloro-9-aminoethylamino-acridine, p-aminobenzoic acid ethylester (and, if desired, esterifying with diethylaminoethanol), p-aminobenzoic acid b -diethylaminoethylester, p-aminobenzoic acid 1 : 2-dimethyl - 3 - dimethylaminopropylester, 6-methoxy - 8 - aminoethylamino - quinoline, 6 - methoxy - 8 - aminopropylamino - quinoline and 6 - methoxy - 8 - amino - n - butylaminoquinoline; (3) a -aceto-b -methylbutyrolactone with 6-methoxy-8-aminoethylamino-quinoline, 6-methoxy-8-amino-n-butylamino-quinoline and 6 - methoxy - 8 - amino - n - pentylaminoquinoline; (4) a -propionylbutyrolactone with 6-methoxy-8-amino-n-butylamino-quinoline; (5) a - aceto - b - hydroxymethy-butyrolactone with 6 - methoxy - 8 - aminopropylaminoquinoline. Butyrolactone derivatives.--The b -methyl and b -hydroxymethyl derivatives of a -acetobutyrolactone are obtained by reacting acetoacetic ester with propylene oxide and glycide respectively. a -Propionyl-butyrolactone is prepared by reacting upon propionylacetic acid ethylester with ethylene oxide. 6 - Methoxy - 8 - aminoalkylamino - quinolines, used in the above examples, are prepared by treating 6-methoxy-8-aminoquinoline with the corresponding o -bromalkyl-phthalimides and saponifying. 6-Amino-8-b -diethylaminoethoxy-quinoline is obtained by reacting upon 6-amino-8-hydroxyquinoline with b -diethylaminoethyl chloride in alkaline solution. 2 - Methoxy - 6 - chloro - 9 - aminoethylaminoacridine is formed by saponifying the reaction product of 2 - methoxy - 6 : 9 - dichloroacridine with b -aminoethylphthalimide.
GB1936535A 1935-06-28 1935-07-06 Process for the manufacture of condensation products containing nitrogen Expired GB459453A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DEI52656D DE663375C (en) 1935-06-28 1935-06-28 Process for the preparation of nitrogen-containing condensation products
GB1936535A GB459453A (en) 1935-07-06 1935-07-06 Process for the manufacture of condensation products containing nitrogen

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1936535A GB459453A (en) 1935-07-06 1935-07-06 Process for the manufacture of condensation products containing nitrogen

Publications (1)

Publication Number Publication Date
GB459453A true GB459453A (en) 1937-01-06

Family

ID=10128112

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1936535A Expired GB459453A (en) 1935-06-28 1935-07-06 Process for the manufacture of condensation products containing nitrogen

Country Status (1)

Country Link
GB (1) GB459453A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2577900A (en) * 1947-06-20 1951-12-11 George F Lisk Process for producing anils

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2577900A (en) * 1947-06-20 1951-12-11 George F Lisk Process for producing anils

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