GB766512A - Preparation of organic nitriles - Google Patents

Preparation of organic nitriles

Info

Publication number
GB766512A
GB766512A GB3992/55A GB399255A GB766512A GB 766512 A GB766512 A GB 766512A GB 3992/55 A GB3992/55 A GB 3992/55A GB 399255 A GB399255 A GB 399255A GB 766512 A GB766512 A GB 766512A
Authority
GB
United Kingdom
Prior art keywords
nitrile
chloride
oxytetracycline
halide
chlorotetracycline
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
GB3992/55A
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.)
Pfizer Inc
Original Assignee
Pfizer Inc
Charles Pfizer and Co Inc
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 Pfizer Inc, Charles Pfizer and Co Inc filed Critical Pfizer Inc
Publication of GB766512A publication Critical patent/GB766512A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides

Abstract

The invention comprises the nitriles of tetracycline, oxytetracycline and chlorotetracycline, and their preparation from the antibiotics (i.e. CONH2-->CN) by treatment with an acid halide and a normally liquid organic base. The acid halide may be an aryl sulphonyl, aryl carboxylic or carbonyl halide and the antibiotic may be used in the form of salt. The organic base may be used in excess (e.g. 2 mol. per mol. of antibiotic) to serve as reaction medium, addition of the halide being made at such a rate that the temperature does not exceed 60-70 DEG C. A different inert solvent may however be employed. Suitable acid halides are benzenesulphonyl chloride, naphthalenesulphonyl chloride, benzoyl chloride, dinitrobenzoyl chloride and phosgene. Esterification of hydroxyl groups often occurs simultaneously, these being subsequently hydrolysed back to free hydroxyl groups. Alternatively the products may be subsequently esterified and/or the nitrile groups reduced to amino and acylated. Examples show the production of O - benzenesulphonyl - oxytetracycline nitrile and its triacetate, chlorotetracycline nitrile and oxytetracycline nitrile.
GB3992/55A 1954-02-19 1955-02-10 Preparation of organic nitriles Expired GB766512A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US766512XA 1954-02-19 1954-02-19

Publications (1)

Publication Number Publication Date
GB766512A true GB766512A (en) 1957-01-23

Family

ID=22133371

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3992/55A Expired GB766512A (en) 1954-02-19 1955-02-10 Preparation of organic nitriles

Country Status (1)

Country Link
GB (1) GB766512A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1534300A4 (en) * 2002-07-12 2008-04-23 Paratek Pharm Innc 3, 10, and 12a substituted tetracycline compounds

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1534300A4 (en) * 2002-07-12 2008-04-23 Paratek Pharm Innc 3, 10, and 12a substituted tetracycline compounds
US7825105B2 (en) 2002-07-12 2010-11-02 Paratek Pharmaceuticals, Inc. 3, 10, and 12a substituted tetracycline compounds
EP2345637A3 (en) * 2002-07-12 2012-02-15 Paratek Pharmaceuticals, Inc. 3, 10, and 12a substituted tetracycline compounds
US8481513B2 (en) 2002-07-12 2013-07-09 Paratek Pharmaceuticals, Inc. 3, 10, and 12a substituted tetracycline compounds

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