GB804880A - Isocamphane compounds and their preparation - Google Patents

Isocamphane compounds and their preparation

Info

Publication number
GB804880A
GB804880A GB2168/58A GB216858A GB804880A GB 804880 A GB804880 A GB 804880A GB 2168/58 A GB2168/58 A GB 2168/58A GB 216858 A GB216858 A GB 216858A GB 804880 A GB804880 A GB 804880A
Authority
GB
United Kingdom
Prior art keywords
isocamphane
acid
sulphonic
formylamino
sulphonic acids
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
GB2168/58A
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.)
Merck and Co Inc
Original Assignee
Merck 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 Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB804880A publication Critical patent/GB804880A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00Compounds containing amino groups bound to a carbon skeleton
    • C07C211/33Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C211/34Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
    • C07C211/38Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing condensed ring systems

Landscapes

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

Abstract

The invention comprises (1) an isocamphane compound having the general formula: <FORM:0804880/IV (b)/1> in which R0 is an acyl radical derived from a C1-8 carboxylic acid and R1 is a hydrogen atom or a C1-8 alkyl group; (2) a process for producing 3-(N-formylamino)-isocamphane by contacting camphene with hydrogen cyanide in the presence of sulphuric acid or a sulphonic acid; (3) a process for producing 3-aminoisocamphane by reacting 3 - (N - formylamino) - isocamphane with a base; (4) a process for producing compounds of the above formula in which R1 is a hydrogen atom by reacting 3-aminoisocamphane with an acylating agent. In process (2) the reaction may be effected under anhydrous conditions, e.g. in glacial acetic acid using a cyanide salt and in the temperature range 0-5 DEG C. Examples of suitable sulphonic acids are methane sulphonic acid, ethane sulphonic acid, benzene sulphonic acids, toluene sulphonic acids, and naphthalene sulphonic acids; process (3) may be effected by refluxing in aqueous methanol solution and using sodium or potassium hydroxide. In process (4) the acylating agent may be the acid chloride, the acid itself or its anhydride, and the acylation may be effected in the presence of sulphuric acid. Examples describe the preparation of 3-(N - formylamino) - isocamphane, 3 - amino-isocamphane, 3 - acetamido - isocamphane, 3-(N - ethyl - N - acetylamino) - isocamphane, 3-(N - butyrylamino) - isocamphane and 3 - (N-3,3 - dimethylbutyrylamino) - isocamphane. Also mentioned are N-propionyl, N-hexanoyl, N-octanoyl, and N-isopropionyl derivatives of isocamphane.
GB2168/58A 1955-06-06 1956-05-29 Isocamphane compounds and their preparation Expired GB804880A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US804880XA 1955-06-06 1955-06-06

Publications (1)

Publication Number Publication Date
GB804880A true GB804880A (en) 1958-11-26

Family

ID=22157701

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2168/58A Expired GB804880A (en) 1955-06-06 1956-05-29 Isocamphane compounds and their preparation

Country Status (2)

Country Link
GB (1) GB804880A (en)
MY (1) MY6100100A (en)

Also Published As

Publication number Publication date
MY6100100A (en) 1961-12-31

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