GB643974A - Improvements in or relating to the production of phenanthridine compounds - Google Patents

Improvements in or relating to the production of phenanthridine compounds

Info

Publication number
GB643974A
GB643974A GB6191/46A GB619146A GB643974A GB 643974 A GB643974 A GB 643974A GB 6191/46 A GB6191/46 A GB 6191/46A GB 619146 A GB619146 A GB 619146A GB 643974 A GB643974 A GB 643974A
Authority
GB
United Kingdom
Prior art keywords
chloride
dinitro
nitrobenzene
converted
phosphorus
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
GB6191/46A
Inventor
Harry James Barber
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.)
May and Baker Ltd
Original Assignee
May and Baker Ltd
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 May and Baker Ltd filed Critical May and Baker Ltd
Priority to GB6191/46A priority Critical patent/GB643974A/en
Publication of GB643974A publication Critical patent/GB643974A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
    • C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
    • C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst

Landscapes

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

Abstract

9-Phenylphenanthridines (which may contain nitro groups) are made by (1) heating a 2-benzamido-diphenyl unsubstituted in the 21- or 61-position with a pentavalent phosphorus chloride or bromide in an organic ionizing solvent to form an imino halide, which is then cyclized in situ to the phenanthridine by heating to at least 195 DEG C. in an organic non-hydroxylic ionizing solvent medium and in the presence of an inorganic halide catalyst until evolution of hydrogen halide has ceased, or (2) in a single stage, by heating the 2-benzamidodiphenyl with phosphorus oxychloride in an organic non-hydroxylic ionizing solvent medium at at least 200 DEG C. till evolution of hydrogen halide has ceased. The inorganic halide referred to must be zinc, aluminium, stannic, bismuth, mercurous, mercuric, tantalum, ferric, or zirconium chlorides, or phosphorus or bismuth oxychlorides. Solvents specified are nitrobenzene and nitrotoluene. The products may be converted to quaternary salts without isolation from the reaction mixture. In examples: 4.41-dinitro-2-(a -chlorobenzal)-aminodiphenyl is ringclosed to 2.7-dinitro-9-phenylphenanthridine in nitrobenzene using (1) ferric chloride; (2) stannic chloride; (3) aluminium chloride; (4) zinc chloride, and (5) phosphorus oxychloride. Also in examples (6) 4.41-dinitro-2-aminodiphenyl is benzoylated in nitrobenzene, converted to the iminochloride with phosphorus pentachloride, and ringclosed with stannic chloride, giving 2.7-dinitro-9-phenyl-phenanthridine, which is converted to the quaternary sulphate with dimethyl sulphate, and from sulphate to chloride with sodium chloride. Also in examples, the following bodies are converted to their iminochlorides with phosphorus oxychloride, and ringclosed with stannic chloride; (7) 4.41-dinitro-2-benzamidodiphenyl; (8) 41-nitro-2-(m or p-nitrobenzamido)-diphenyl; (9) 4.41-dinitro-2-(p-nitrobenzamide). Finally, (10) 4.41-dinitro-2-benzamidodiphenyl is heated at 210 DEG C. with phosphorus oxychloride in nitrobenzene in one stage. Specifications 372,859, 511,353, 520,273, 577,990 and 587,673 are referred to.
GB6191/46A 1946-02-27 1946-02-27 Improvements in or relating to the production of phenanthridine compounds Expired GB643974A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB6191/46A GB643974A (en) 1946-02-27 1946-02-27 Improvements in or relating to the production of phenanthridine compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB6191/46A GB643974A (en) 1946-02-27 1946-02-27 Improvements in or relating to the production of phenanthridine compounds

Publications (1)

Publication Number Publication Date
GB643974A true GB643974A (en) 1950-10-04

Family

ID=9810078

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6191/46A Expired GB643974A (en) 1946-02-27 1946-02-27 Improvements in or relating to the production of phenanthridine compounds

Country Status (1)

Country Link
GB (1) GB643974A (en)

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