GB595603A - Process for the production of arylamino acridine derivatives - Google Patents
Process for the production of arylamino acridine derivativesInfo
- Publication number
- GB595603A GB595603A GB1593444A GB1593444A GB595603A GB 595603 A GB595603 A GB 595603A GB 1593444 A GB1593444 A GB 1593444A GB 1593444 A GB1593444 A GB 1593444A GB 595603 A GB595603 A GB 595603A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenol
- primary
- heated
- acridine
- cyano
- 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
Links
- -1 arylamino acridine derivatives Chemical class 0.000 title abstract 4
- 229940027998 antiseptics and disinfectants Acridine derivatives Drugs 0.000 title abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 8
- 150000001251 acridines Chemical class 0.000 abstract 3
- 150000004982 aromatic amines Chemical class 0.000 abstract 3
- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 239000000376 reactant Substances 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- DXGRQSKRHQCNMS-UHFFFAOYSA-N COC1=CC=C2N=C3C=CC(=CC3=C(C2=C1)Cl)C#N Chemical compound COC1=CC=C2N=C3C=CC(=CC3=C(C2=C1)Cl)C#N DXGRQSKRHQCNMS-UHFFFAOYSA-N 0.000 abstract 1
- 210000004940 Nucleus Anatomy 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004432 carbon atoms Chemical group C* 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- 150000001896 cresols Chemical class 0.000 abstract 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000006011 modification reaction Methods 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic 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
- C07D219/08—Nitrogen atoms
- C07D219/10—Nitrogen atoms attached in position 9
Abstract
Monocyclic arylamino acridine derivatives having the general formula <FORM:0595603/IV/1> in which R1 represents a monocyclic aryl group containing a cyano group in the o-m m- or p-position and R2 represents hydrogen or an alkyl or substituted alkyl (e.g. hydroxyalkyl alkoxyalkyl or dialkylaminoalkyl) group, are obtained by treating a meso-halogenated acridine with a primary or secondary monocyclic arylamine of the general formula NHR1R2. When a primary arylamine is used the reactants may be heated in an excess of a phenol, e.g. phenol itself or a mixture of the isomeric cresols or higher alkylated phenols, but in a modification of this method the mesohalogenated acridine and the phenol may first be heated and the product, with or without isolation, then heated with the primary arylamine in phenol; otherwise the reactants may be in solution in an alkanol containing up to eight carbon atoms, preferably anhydrous and in the presence of a small amount of copper powder. Numerous examples are given. Specified starting materials are primary or secondary arylamines: N-monoalkyl substituted aminobenzonitriles, and aminobenzonitriles containing one or more additional nuclear substituents. In general, the acridines may contain one or more nuclear substituents such as alkyl, alkoxy, nitro, amino, substituted amino, cyano and halogen in either or both of the benzenoid nuclei. 7 - Methoxy - 2 - cyano - 9 - chloroacridine is obtainable by treating 41-methoxy-4-cyanodiphenylamine-2-carboxylic acid with phosphorus oxychloride.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB595603A true GB595603A (en) | 1947-12-10 |
Family
ID=1731929
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1593444A Expired GB595603A (en) | 1944-08-21 | Process for the production of arylamino acridine derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB595603A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0405342A1 (en) * | 1989-06-26 | 1991-01-02 | Hoechst-Roussel Pharmaceuticals Incorporated | (1,2,3,4-Tetrahydro-9-acridinimino)cyclohexane carboxylic acid and related compounds, a process for their preparation and their use as medicaments |
-
1944
- 1944-08-21 GB GB1593444A patent/GB595603A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0405342A1 (en) * | 1989-06-26 | 1991-01-02 | Hoechst-Roussel Pharmaceuticals Incorporated | (1,2,3,4-Tetrahydro-9-acridinimino)cyclohexane carboxylic acid and related compounds, a process for their preparation and their use as medicaments |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB700044A (en) | Process for the preparation of new anthraquinone derivatives | |
| GB595603A (en) | Process for the production of arylamino acridine derivatives | |
| GB826641A (en) | 1-phenyl-3-halogeno-5-piperazino-pyridazine-(6) compounds, and a process for their manufacture | |
| GB604279A (en) | Production of substituted arylamino acridine derivatives | |
| GB1100960A (en) | 1,4-benzodioxane derivatives | |
| Birch | 83. A new reagent for primary and secondary aliphatic amines | |
| GB744972A (en) | Manufacture of triphenylmethane dyestuffs | |
| US2816900A (en) | Preparation of methyl violet | |
| GB611316A (en) | Process for the preparation of diarylamines | |
| GB1100219A (en) | A process for the preparation of 3-nitro-4-halophenol derivatives | |
| GB997476A (en) | Process for the manufacture of linear quinacridones | |
| ES322224A1 (en) | Processes for the manufacture of disazo pigments | |
| GB593753A (en) | Improvements in or relating to the production of cyanoalkylamino derivatives of acridine | |
| SE7605200L (en) | METHOD OF PREPARING 2-SUBSTITUTED 1,4-BENZODIAZEPIN DERIVATIVES | |
| GB920753A (en) | Process for the preparation of di-benzoxazolyl-ethylene compounds | |
| US2269652A (en) | Method for the preparation of isocytosine | |
| ES305155A1 (en) | New disazo pigments and processes for their manufacture | |
| GB611476A (en) | Improvements in and relating to the production of secondary diamines | |
| US2401268A (en) | Production of nitrolic acids and pseudonitroles | |
| US2493578A (en) | Cyanoalkylamino derivatives of acridine and method for their production | |
| ES412088A1 (en) | Pyridoquinoline derivatives | |
| GB1037894A (en) | New isourea derivatives and process for the production thereof | |
| GB601768A (en) | Process for the manufacture of derivatives of acridine | |
| US2287155A (en) | Phosphoric acid dichlorides of 4-amino benzene sulphonamide and process for the manufacture of same | |
| GB735890A (en) | New pyrimidine derivatives and process for their production |