GB977709A - Hydrazine derivatives and preparation of same - Google Patents

Hydrazine derivatives and preparation of same

Info

Publication number
GB977709A
GB977709A GB4285/61A GB428561A GB977709A GB 977709 A GB977709 A GB 977709A GB 4285/61 A GB4285/61 A GB 4285/61A GB 428561 A GB428561 A GB 428561A GB 977709 A GB977709 A GB 977709A
Authority
GB
United Kingdom
Prior art keywords
bromo
acid
formula
amine
benzyl bromide
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
GB4285/61A
Inventor
David John Drain
Hadyn Windsor Richard Williams
John Gordon Bernard Howes
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.)
Smith and Nephew PLC
TJ Smith and Nephew Ltd
Original Assignee
Smith and Nephew PLC
TJ Smith and Nephew 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 Smith and Nephew PLC, TJ Smith and Nephew Ltd filed Critical Smith and Nephew PLC
Priority to GB4285/61A priority Critical patent/GB977709A/en
Priority to ES0274285A priority patent/ES274285A1/en
Priority to DES77889A priority patent/DE1168919B/en
Priority to FR896214A priority patent/FR2161M/en
Publication of GB977709A publication Critical patent/GB977709A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/10—Hydrazines

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises compounds of general formula <FORM:0977709/C1/1> wherein X represents a halogen atom, n represents 0, 1, 2 or 3, R represents an alkyl (including cycloalkyl) group containing up to 4 carbon atoms, and R1 represents hydrogen or an alkylbenzenesulphonyl or benzenesulphonyl group; their acid addition salts; and their preparation by reduction of a corresponding N-nitrosamine of formula <FORM:0977709/C1/2> (the sulphonyl substituent of which, when present, may be hydrolysed off before or after reduction), the product optionally being isolated in the form of a hydrazone formed from a steam-volatile aldehyde and regenerated by treating this with aqueous acid at elevated temperature and removing the aldehyde so formed by steam distillation. N-Nitrosamines II are prepared by reaction of nitrous acid or of an alkyl nitrite and acid with an amine of formula <FORM:0977709/C1/3> which may be obtained (and hydrochlorides) either by reaction of a corresponding benzyl bromide and amine RNH2 or by hydrogenation and optionally hydrolysis of a Schiff's base of formula <FORM:0977709/C1/4> which may be obtained from a corresponding benzaldehyde and amine. 6-Bromo-N-methyl-3, 4-dihydro-1, 3, 2-benzoxazine is obtained from p-bromo-phenol, methylamine and formaldehyde, and on refluxing with hydrochloric acid in ethanol yields N-(3-bromo-6-hydroxybenzyl)-methylammonium chloride. 3-Benzenesulphonyloxy-benzyl bromide and the 4-bromo-, 6-bromo- and 6-chloro-compounds and 2-benzenesulphonyloxy-3-bromo-benzyl bromide are obtained by irradiation-catalyzed bromination. 2-(p-Toluenesulphonyloxy)-benzaldehyde is prepared from p-toluenesulphonyl chloride and salicylaldehyde. Pharmaceutical compositions which comprise compounds I and the physiologically tolerable acid addition salts with carriers or diluents are mentioned for the treatment of mental disorders. In the second and third Provisional Specifications it is said that R1 may be acyl generally.
GB4285/61A 1961-02-04 1961-02-04 Hydrazine derivatives and preparation of same Expired GB977709A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
GB4285/61A GB977709A (en) 1961-02-04 1961-02-04 Hydrazine derivatives and preparation of same
ES0274285A ES274285A1 (en) 1961-02-04 1962-02-03 Hydrazine derivatives and preparation of same
DES77889A DE1168919B (en) 1961-02-04 1962-02-03 Process for the preparation of hydroxybenzyl hydrazines
FR896214A FR2161M (en) 1961-02-04 1962-05-02 Medicinal product based on hydrazine derivative.

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB4285/61A GB977709A (en) 1961-02-04 1961-02-04 Hydrazine derivatives and preparation of same
GB1983561 1961-06-01
GB4661061 1961-12-29

Publications (1)

Publication Number Publication Date
GB977709A true GB977709A (en) 1964-12-09

Family

ID=10879299

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4285/61A Expired GB977709A (en) 1961-02-04 1961-02-04 Hydrazine derivatives and preparation of same

Country Status (4)

Country Link
DE (1) DE1168919B (en)
ES (1) ES274285A1 (en)
FR (1) FR2161M (en)
GB (1) GB977709A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006169122A (en) * 2004-12-13 2006-06-29 Kuraray Co Ltd Method for producing 2-sulfonyloxyphenylacetic acid derivative

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006169122A (en) * 2004-12-13 2006-06-29 Kuraray Co Ltd Method for producing 2-sulfonyloxyphenylacetic acid derivative

Also Published As

Publication number Publication date
ES274285A1 (en) 1962-05-16
FR2161M (en) 1963-11-25
DE1168919C2 (en) 1964-11-19
DE1168919B (en) 1964-04-30

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