GB729332A - Substituted 4-amino-toluenes - Google Patents

Substituted 4-amino-toluenes

Info

Publication number
GB729332A
GB729332A GB21050/52A GB2105052A GB729332A GB 729332 A GB729332 A GB 729332A GB 21050/52 A GB21050/52 A GB 21050/52A GB 2105052 A GB2105052 A GB 2105052A GB 729332 A GB729332 A GB 729332A
Authority
GB
United Kingdom
Prior art keywords
chloro
aminotoluene
products
substituted
dialkylaminoalkyl
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
GB21050/52A
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.)
Bayer AG
Original Assignee
Bayer 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 Bayer AG filed Critical Bayer AG
Publication of GB729332A publication Critical patent/GB729332A/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
    • C07D295/125—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 attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—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 attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Indole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The invention comprises 4-aminotoluenes substituted in the 2-position by halogen, nitro or cyano, and in the amino group by aminoalkyl and, if desired, a further alkyl, aryl, aralkyl, cycloalkyl or aminoalkyl group. The terminal amino group may be primary, secondary or tertiary, and in the last case may form part of a heterocyclic nucleus. The products may be obtained in various ways. In examples, 2 - chloro - 4 - aminotoluene gives 4 - dialkylaminoalkylamino products by reaction with b -diethylaminoethyl chloride and numerous similar compounds as hydrochlorides, and with b -bromoethylphthalimide, the 4-aminoethylamino-derivative after saponification; 2-bromo-and 2-iodo-substituted 4-aminotoluene derivatives are obtained by similar methods; 2-chloro-4-methyl or ethyl aminotoluene gives N-methyl- or ethyl-N-dialkylaminoalkyl derivatives with b -diethylaminoethyl chloride, b -bromoethyl-phthalimide, and other dialkylaminoalkyl-chlorides; other 2-chloro-4-alkylamino-toluenes give similar N-alkyl-N-dialkylaminoalkyl-derivatives, including the product 2 - chloro - 4 - (N - bis - b - diethylaminoethyl) - aminotoluene; 2 - chloro - 4 - cyclohexylaminotoluene, and 2-chloro-4-(N-benzyl-amino-N-b -diethylamino-ethyl) amino-toluene are also specified; the N-benzyl-group may be substituted in o-, m- and p-positions by Cl and methyl; other products specified include 2-chloro-4-N-phenyl and methoxyphenyl-N-dialkylaminoalkyl-toluene; 2-chloro-4-toluidine is converted into the 4-b -hydroxylethylamino-derivative with glycolchlorhydrin, and thence to the 4-b -chloroethylamino derivative with thionyl chloride; this product reacts with a number of primary, and secondary amines, aminoalcohols and heterocyclic amines, and a b -dialkylamino-alkylamine, and gives corresponding N-substituted products; similar products are obtained by similar methods from 2-nitro and 2-cyano-4-aminotoluene. Specification 433,625 is referred to.
GB21050/52A 1951-08-21 1952-08-21 Substituted 4-amino-toluenes Expired GB729332A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE729332X 1951-08-21

Publications (1)

Publication Number Publication Date
GB729332A true GB729332A (en) 1955-05-04

Family

ID=6635936

Family Applications (1)

Application Number Title Priority Date Filing Date
GB21050/52A Expired GB729332A (en) 1951-08-21 1952-08-21 Substituted 4-amino-toluenes

Country Status (2)

Country Link
FR (1) FR1067944A (en)
GB (1) GB729332A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2953490A (en) * 1957-03-14 1960-09-20 Monsanto Chemicals Propylamine fungicides
US7456222B2 (en) 2002-05-17 2008-11-25 Sequella, Inc. Anti tubercular drug: compositions and methods
US7652039B2 (en) 2002-05-17 2010-01-26 Sequella, Inc. Methods of use and compositions for the diagnosis and treatment of infectious disease
US7884097B2 (en) 2003-09-05 2011-02-08 Sequella, Inc. Methods and compositions comprising diamines as new anti-tubercular therapeutics
US8268894B2 (en) 2002-05-17 2012-09-18 The United States Of America As Represented By The Secretary, Department Of Health And Human Services Compositions and methods for the treatment of infectious diseases
CN101585774B (en) * 2009-06-15 2013-01-09 西南大学 Synthetic method of N-aralkyl anilines compound

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2953490A (en) * 1957-03-14 1960-09-20 Monsanto Chemicals Propylamine fungicides
US7456222B2 (en) 2002-05-17 2008-11-25 Sequella, Inc. Anti tubercular drug: compositions and methods
US7652039B2 (en) 2002-05-17 2010-01-26 Sequella, Inc. Methods of use and compositions for the diagnosis and treatment of infectious disease
US8198303B2 (en) 2002-05-17 2012-06-12 Sequella, Inc. Methods of use and compositions for the diagnosis and treatment of infectious diseases
US8268894B2 (en) 2002-05-17 2012-09-18 The United States Of America As Represented By The Secretary, Department Of Health And Human Services Compositions and methods for the treatment of infectious diseases
US7884097B2 (en) 2003-09-05 2011-02-08 Sequella, Inc. Methods and compositions comprising diamines as new anti-tubercular therapeutics
US8202910B2 (en) 2005-07-01 2012-06-19 Sequella, Inc. Compositions and methods for treatment of infectious disease
CN101585774B (en) * 2009-06-15 2013-01-09 西南大学 Synthetic method of N-aralkyl anilines compound

Also Published As

Publication number Publication date
FR1067944A (en) 1954-06-21

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