GB490364A - Improvements in the manufacture and production of amino compounds - Google Patents

Improvements in the manufacture and production of amino compounds

Info

Publication number
GB490364A
GB490364A GB384437A GB384437A GB490364A GB 490364 A GB490364 A GB 490364A GB 384437 A GB384437 A GB 384437A GB 384437 A GB384437 A GB 384437A GB 490364 A GB490364 A GB 490364A
Authority
GB
United Kingdom
Prior art keywords
acid
dinitrochlorobenzene
aminopropionic
sulphonic
acids
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
GB384437A
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
Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to GB384437A priority Critical patent/GB490364A/en
Publication of GB490364A publication Critical patent/GB490364A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B51/00Nitro or nitroso dyes

Abstract

Reaction is effected between (1) a secondary amine of the formula RNHCH2R1, in which R is an organic radicle, other than an acyl radicle, and -CH2R1 is an aliphatic radicle containing at least one negative substituent, this term being defined to mean a hydroxy, ketonic, carboxylic, sulphonic or nitrile group, and (2) an aromatic nitro compound containing halogen linked directly to the aryl nucleus; the reaction yields tertiary amino compounds by elimination of hydrogen halide between the NH group of reagent (1) and the halogen atom of reagent (2). Suitable reagents of type (1) are N-alkyl-o - aminoalkylene carboxylic and sulphonic acids, such as N-methyl-, N-ethyl-, N-propyl-, N-butyl-, N-dodecyl-, N-octadecyl-, N-oleyl- or N - cyclohexyl - b - aminopropionic acid or -b -aminoethanesulphonic acid, N-aryl-b -aminopropionic acids such as N-phenyl- or N-naphthyl-b -aminopropionic acids, N-phenyl- or N-naphthyl-b -aminoethanesulphonic acids and similarly substituted aminopropanesulphonic acids or aminohydroxypropanesulphonic acids, N - hydroxyethylaniline, N - b ,g - dihydroxypropylaniline, and N-b -hydroxy-g -ethoxypropylaniline; the amine may contain other substituents such as a nitro, alkyl, alkoxy, acetyl-amino or tertiary amino group, and when the amine contains an aryl radicle, the latter may be substituted by a thiosulphonic group or any of the substituents specified above, such as a carboxylic or sulphonic group; in any event, however, the amine must not contain a primary amino group or an additional secondary amino group. Suitable reagents of type (2) are 2 - nitrochlorobenzene, 2 : 4 - dinitrochlorobenzene, 4-nitrochlorobenzene-2-sulphonic acid, 2 - nitrochlorobenzene - 4 - sulphonic acid, 2 : 4-dinitrochlorobenzene - 6 - sulphonic acid, 2 : 4-dinitrochlorobenzene - 6 - carboxylic acid, 2 : 6-dinitrochlorobenzene - 4 - carboxylic acid, 1-chloro-2 : 4-dinitronaphthalene, 1 : 3-dichloro-4 : 6-dinitrobenzene, 2 : 6-dichloro-3 : 5-dinitro-toluene, and compounds of the type RXR, in which R is 3-nitro-4-halogenphenyl and X is a -CO-, -SO2-, -CH2-, -NH-, -CH2 CH2-, or -CH : CH- group. The reaction may be effected by heating the reagents to 60-200 DEG at atmospheric or raised pressure in the presence or absence of a solvent or diluent, an acid-binding agent and/or a catalyst : the latter may be copper acetate or borate or copper powder. Some of the products are useful as dyes, and others as intermediates for dyes. Examples are given in which (1) N-m-tolyl-b -aminopropionic acid (from m-toluidine and acrylic acid) and 2 : 4-dinitrochlorobenzene yield N - m - tolyl - N - (2 : 4 - dinitrophenyl) - b -aminopropionic acid; N - (4-methoxyphenyl)-N-(2 : 4 - dinitrophenyl) - b - aminopropionic acid and N - (2-methoxy-5-methylphenyl)-N-(2 : 4-dinitrophenyl) - b - aminopropionic acid are similarly obtainable from 2 : 4-dinitrochlorobenzene and, respectively, N - (4 - methoxyphenyl)-b -aminopropionic acid (from p-anisidine and acrylic acid) and N-(2-methoxy-5-methyl)-b -aminopropionic acid (from 2-methoxy-5-methylaniline and acrylic acid); corresponding products are obtainable from N-phenyl-b -aminopropionic acid or its substitution products, or N-cyclohexyl-b -aminopropionic acid, and also from carboxylic or sulphonic acids of 2 : 4-dinitrochlorobenzene; (2) N-(1-naphthyl)-b -aminopropionic acid (from 1-naphthylamine and acrylic acid) and 2 : 4-dinitrochlorobenzene yield N-(1-naphthyl)-N-(2 : 4-dinitrophenyl)-b -aminopropionic acid; corresponding products are obtainable from N-(2-naphthyl)-b -aminopropionic acid or substituted N-naphthyl-b -aminopropionic acids, and also from carboxylic or sulphonic acids of 2 : 4-dinitrochlorobenzene; (3) N-phenyl-b -aminopropionic acid and 2 : 6-dinitrochlorobenzene-4-sulphonic acid yield N-phenyl- N - (2 : 6- dinitro - 4 - sulphophenyl)- b -aminopropionic acid; (4) N-butyl-b -aminopropionic acid (from n-butylamine and acrylic acid) and 2 : 4-dinitrochlorobenzene yield N-butyl-N-(2 : 4 - dinitrophenyl) - b - aminopropionic acid; (5) N-o-tolyl-b -aminopropionic acid (from o-toluidine and acrylic acid) and 1 : 3-dichloro-2 : 4 - dinitrobenzene yield a product of unspecified constitution; (6) N-phenyl-b -aminoethanesulphonic acid and 2 : 4-dinitrochlorobenzene-6-carboxylic acid yield N-phenyl-N-(2 : 4-dinitro-6-carboxyphenyl)-b -aminoethanesulphonic acid; the product dyes wool in reddish-brown shades; corresponding products are obtainable from substituted N-phenylaminoethanesulphonic acids and 2 : 4-dinitrochlorobenzene-6-carboxylic (or sulphonic) acid; (7) N - (4 - methoxyphenyl) - b - aminopropionic acid (2 mols.) and 4 : 41-dichloro-3 : 31-dinitrodiphenylsulphone (1 mol.) yield N : N1-di(4-methoxyphenyl) - N : N1 - di(b - carboxyethyl)-4 : 41-diamino - 3 : 31-dinitrodiphenylsulphone; corresponding products are obtainable from 4 : 41-dichloro-3 : 31-dinitrobenzophenone and from N - (4 - methoxyphenyl) - b - aminoethanesulphonic acid; the products dye wool in reddish-brown shades; (8) N-hydroxyethylaniline and 2 : 4 - dinitrochlorobenzene - 6-sulphonic acid yield a product of unspecified constitution, which dyes wool in bluish-grey shades; a yellow dye is similarly obtainable from N-phenyl-b -aminopropionitrile and 2 : 4-dinitrochlorobenzene-6-sulphonic acid; (9) N-phenylglycine and 2 : 4-dinitrochlorobenzene yield N-phenyl-N-(2 : 4-dinitrophenyl)glycine; corresponding products are obtainable from N-(o-carboxyphenyl)glycine and from other nitrohalogenbenzenes. A sample has been furnished under Sect. 2(5), of N - (g - oxobutyl) - N - (2 : 4 - dinitrophenyl)-aniline, obtained by condensing N-(g -oxobutyl)-aniline with 2 : 4-dinitrochlorobenzene.
GB384437A 1937-02-09 1937-02-09 Improvements in the manufacture and production of amino compounds Expired GB490364A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB384437A GB490364A (en) 1937-02-09 1937-02-09 Improvements in the manufacture and production of amino compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB384437A GB490364A (en) 1937-02-09 1937-02-09 Improvements in the manufacture and production of amino compounds

Publications (1)

Publication Number Publication Date
GB490364A true GB490364A (en) 1938-08-09

Family

ID=9765994

Family Applications (1)

Application Number Title Priority Date Filing Date
GB384437A Expired GB490364A (en) 1937-02-09 1937-02-09 Improvements in the manufacture and production of amino compounds

Country Status (1)

Country Link
GB (1) GB490364A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2454835A (en) * 1943-03-29 1948-11-30 Parke Davis & Co N-propyl diaminodiphenylsulfone and process for obtaining same
US2589211A (en) * 1948-11-23 1952-03-18 Parke Davis & Co Aminophenylsulfonylphenylamino-alkanoic acids
US2623063A (en) * 1948-09-20 1952-12-23 Schering Corp Chemotherapeutic compounds
US5068250A (en) * 1988-09-29 1991-11-26 Trustees Of University Of Pennsylvania Irreversible ligands for nonsteroidal antiinflammatory drug and prostaglandin binding sites
US5187187A (en) * 1988-09-29 1993-02-16 Trustees Of The University Of Pennsylvania Irreversible ligands for nonsteroidal antiinflammatory drug and prostaglandin binding sites

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2454835A (en) * 1943-03-29 1948-11-30 Parke Davis & Co N-propyl diaminodiphenylsulfone and process for obtaining same
US2623063A (en) * 1948-09-20 1952-12-23 Schering Corp Chemotherapeutic compounds
US2589211A (en) * 1948-11-23 1952-03-18 Parke Davis & Co Aminophenylsulfonylphenylamino-alkanoic acids
US5068250A (en) * 1988-09-29 1991-11-26 Trustees Of University Of Pennsylvania Irreversible ligands for nonsteroidal antiinflammatory drug and prostaglandin binding sites
US5187187A (en) * 1988-09-29 1993-02-16 Trustees Of The University Of Pennsylvania Irreversible ligands for nonsteroidal antiinflammatory drug and prostaglandin binding sites

Similar Documents

Publication Publication Date Title
US2212825A (en) Nitro-trifluoromethyl-aryl amines and process for making them
GB490364A (en) Improvements in the manufacture and production of amino compounds
GB1113809A (en) Azo dyestuffs and their metal complex compounds and process for preparing them
US3231601A (en) Process for the cyanoethylation of aromatic amines
US2046356A (en) Manufacture of diarylamine derivatives
GB805562A (en) New phthalocyanine compounds
GB837953A (en) New monoazo triazine dyestuffs
DE2425314C2 (en) Process for the reduction of nitroanthraquinone compounds
DE2825594C2 (en)
GB838311A (en) New copper-containing triazine monoazo dyestuffs
GB779880A (en) Functional derivatives of azo-dyestuffs containing sulphonic acid groups and processfor making them
GB749308A (en) Manufacture of triphenylmethane dyestuffs
US2109183A (en) Process for the manufacture of azo dyestuffs
GB815746A (en) Process for the manufacture of dioxy-nitro-arylaminoanthraquinones and the products obtained thereby
GB980232A (en) Improvements relating to cyclic azo compounds
US1872033A (en) Fast azo dye
US2051005A (en) Process of producing n-substitution products of 1, 4-diaminoanthraquinones
JPS6354704B2 (en)
US2572067A (en) Trifluoromethyl diphenylamines
US2150001A (en) Manufacture of di-(gamma-chlorohydroxypropyl) arylamines
GB965235A (en) Pyridino-anthrone dyes and dye intermediates
GB838728A (en) New disazo triazine dyestuffs
GB580351A (en) New dyestuffs of the anthraquinone series
US2443255A (en) Derivatives of 2-aminc-diphenylsulfone
US2032635A (en) Black sulphur dyestuffs