GB437953A - Process for the manufacture of acridine derivatives - Google Patents

Process for the manufacture of acridine derivatives

Info

Publication number
GB437953A
GB437953A GB1355934A GB1355934A GB437953A GB 437953 A GB437953 A GB 437953A GB 1355934 A GB1355934 A GB 1355934A GB 1355934 A GB1355934 A GB 1355934A GB 437953 A GB437953 A GB 437953A
Authority
GB
United Kingdom
Prior art keywords
product
group
prepared
acid
diethylamino
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
GB1355934A
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 GB1355934A priority Critical patent/GB437953A/en
Publication of GB437953A publication Critical patent/GB437953A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D219/00Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/04Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 carbon atoms of the ring system
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D219/00Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/04Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 carbon atoms of the ring system
    • C07D219/08Nitrogen atoms
    • C07D219/10Nitrogen atoms attached in position 9
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D219/00Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/04Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 carbon atoms of the ring system
    • C07D219/08Nitrogen atoms
    • C07D219/10Nitrogen atoms attached in position 9
    • C07D219/12Amino-alkylamino radicals attached in position 9

Landscapes

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

Abstract

9-Aminoacridines substituted in the amino group by basic substituents of the type defined in the parent Specification and containing in the 6-position a halogen atom or an alkyl group and in the 2-position an alkylmercapto group are prepared (a) by reacting upon such acridine derivatives as contain as a reactive substituent in the 9-position a halogen, alkoxy, aryloxy, mercapto, substituted mercapto or sulpho group, a halogen atom or an alkyl group in the 6 - position and an alkylmercapto in the 2-position with a base or salt thereof which contains at least two nitrogen atoms at least one of which is in a primary or secondary amino group; (b) by reacting an acridine derivative as in (a) with a base or salt thereof which contains at least two nitrogen atoms, one of which is substituted by an acyl residue, and splitting off the acyl residue by saponification; (c) by reacting an acridine as in (a) with an aminoalcohol or with an aminohalogen alkyl compound and further reacting the product with ammonia or a primary or secondary amine, if necessary after the esterification of the hydroxy group to give a basically substituted 9-amino derivative; (d) by reacting an acridine derivative as specified in (a) except that the 6-position is occuped by a nitro or amino group and/or the 2-position by a mercapto group, so as to introduce a basic radicle in 9-position and then converting the 6-nitro (with prior reduction) or amino group to a halogen substituent by a Sandmeyer process and/or the 2-mercapto to an alkylmercapto group by alkylation; (e) by subjecting a diphenylamine-6-carboxylic acid amide basically substituted in the amide group and containing in the 3-position a halogen atom or an alkyl group or a nitro or amino group and in the 4<1>-position an alkylmercapto or mercapto group to ring closure, a nitro or amino group in the 6-position and a mercapto group in the 2-position being converted into halogen and alkylmercapto respectively by the processes referred to in (d). The basic residue attached to the 9-amino group may contain one or more nitrogen atoms, also ether or thioether linkages or hydroxy groups and may be aliphatic, isocyclic, or heterocyclic in character. In examples: (1) 2.4-dichlorobenzoic acid is condensed with 4-aminothiophenolmethylether, the product ring-closed and chlorinated to give 2 - methylmercapto - 6.9-dichloracridine; this is condensed with a -diethylamino - d - aminopentane, a -diethylamino-d -aminobutane, b -diethylaminoethoxyethylamine, b - diethylaminoethylmercaptoethylamine; (2) 2.4-dichlorbenzoic acid is condensed with 4-aminothiophenolethylether, the product ring-closed and chlorinated to give 2-ethylmercapto-6.9-dichloracridine which is condensed with a -diethylamino-d -aminopentane, and with a -diethylamino-g -aminopropane; (3) 4-methyl-2-chlorbenzoic acid is condensed with 4-aminothiophenol methylether, the product ring-closed and chlorinated to give 2-methylmercapto - 6 - methyl - 9 - chloracridine which is condensed with a -diethylamino-d -aminopentane, a -diethylamino-b .b -dimethyl-g -aminopropane and with a - diethylamino - e -aminopentane; 2-butylmercapto-6.9-dichloracridine (prepared by condensing 4-butylmercapto-1-aminobenzene with 2.4-dichlorbenzoic acid and ring-closing and chlorinating the product) is condensed with a -diethylamino-d -aminopentane; 2-isooctylmercapto-6.9-dichloracridine (prepared by condensing 4-isooctylmercapto-1-aminobenzene with 2.4-dichlorbenzoic acid and ring-closing and chlorinating the product) is condensed with a -diethylamino-d -aminopentane. Most of these compounds are isolated in the form of their salts with organic acids (picric, citric, methylene-disalicylic acids). Samples have been furnished under Sect. 2 (5) of the following products: (I) 2-methylmercapto - 6 - chloro - 9 - (p - aminomethylphenyl)-aminoacridine prepared by condensing 2-methylmercapto-6.9-dichloracridine with phenol and the resulting 9-phenoxy derivative with N-(4-aminobenzyl) - acetamide; the product is saponified by means of hydrochloric acid; (II) 2-methylmercapto-6-chloro-9-(p-diethylaminoethyloxyphenyl) - aminoacridine prepared by reacting 2-methylmercapto-6.9-dichloracridine with phenol and 4-aminophenylhydroxyethylether, treating the product with thionyl chloride and then with diethylamine; (III) the same product as (II) prepared by condensing 4-aminothiophenol-methylether with 4-nitro-2-chlorbenzoic acid, ring-closing and chlorinating to give 2 - methylmercapto - 6 - nitro - 9 - chloracridine, reacting this with 4-aminophenyldiethylaminoethylether, reducing the product with iron in acetic acid, diazotizing and finally treating this diazo body with cuprous chloride; (IV) 2-methylmercapto-6-chloro-9-(p-diethylaminoethylmercaptophenyl -aminoacridine prepared by condensing 4-aminothiophenol-methylether with 2.4-dichlorbenzoic acid, treating the product with phosphorus pentachloride and condensing the product with 4-aminothiophenyldiethylaminoethylether; the acid amide product obtained is ring-closed by heating with phosphorus oxychloride. Specification 267,169, [Class 2 (iii)], also is referred to. N-(4-aminobenzyl)-acetamide is prepared by reducing the corresponding nitro derivative with iron in acetic acid. 4-Aminophenylhydroxyethylether is prepared by reacting potassium 4-nitrophenolate with chlorethylalcohol and reducing with iron in acetic acid. 4-Aminothiophenol-diethylaminoethylether is prepared by boiling 4.4<1>-dinitrodiphenyl-disulphide with alcoholic sodium ethylate, condensing the product with diethylaminoethylchloride and reducing by means of iron in acetic acid.
GB1355934A 1934-05-04 1934-05-04 Process for the manufacture of acridine derivatives Expired GB437953A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1355934A GB437953A (en) 1934-05-04 1934-05-04 Process for the manufacture of acridine derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1355934A GB437953A (en) 1934-05-04 1934-05-04 Process for the manufacture of acridine derivatives

Publications (1)

Publication Number Publication Date
GB437953A true GB437953A (en) 1935-11-04

Family

ID=10025128

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1355934A Expired GB437953A (en) 1934-05-04 1934-05-04 Process for the manufacture of acridine derivatives

Country Status (1)

Country Link
GB (1) GB437953A (en)

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