Patent GB-999806-A (GB)
Title: New 1,2-dihydroquinoline derivatives
Inventor: BROWN JOSEPH PATRICK
IPC: C07D215/20
Filed: 1962-10-30
Abstract: The invention comprises 4-substituted-aliphatic - 2,2 - dialiphatic - 1,2 - dihydroquinolines and slats thereof in which the 4-substituent is an alkoxy, thiocyano, mercapto, amino, hydroxyl, aryloxy, arylthio, thiazolethio, cyano, dithiocarbamyl, isothiuronium, acetoacetate or malonic ester group, in which one or more of the positions 5 to 8 of the dihydroquinoline nucleus can optionally contain as a substituent a halogen atom or an alkoxy, hydroxy, amino, nitro, aliphatic or aromatic group, and in which a halogen atom can optionally be present as a substituent in the 3-position, and compounds containing two 2,2-dialiphatic-1,2-dihydroquinol-4-ylaliphatic radicals and salts thereof in which the linking groups are N,N-amino, N,N1-diamino, O,O1-glycol, S,S1-dithio, or S,S1-bis (dithiocarbamate) and each dihydroquinoline nucleus can contain substituents in positions 5 to 8 and position 3 as stated above.  The invention further comprises a process for the preparation of 2,2-dialiphatic - 1,2 - dihydroquinoline derivatives, wherein one or more 2,2-dialiphatic-1,2-dihydroquinol-4-yl-aliphatic radicals are linked to an atom or group derived from a nucleophilic reagent, or salts thereof, in which a 4-halogeno-aliphatic - 2,2 - dihydroquinoline is reacted with the nucleophilic reagent.  The hydroquinolines of the invention can be the free secondary bases, tertiary bases, N-acylated secondary bases, and acid addition and quaternary ammonium salts of the secondary and tertiary bases. It is preferred that the process of the invention be effected in the presence of inert solvents at an elevated temperature, e.g. 40-50 DEG  C.  Salts can be obtained by treating the free base with an appropriate reagent and N-acylated derivatives by acylation of the free base.  The 4-halogeno aliphatic reactants are described in Specification 945,330 and the nucleophilic agent is one that is appropriate to the desired product.  Said process may be employed to produce compounds other than those of the invention, e.g. the replacement of the halogen atom in the 4-halogeno-aliphatic reactant by a different halogen atom.  The term "aliphatic" as used above includes cycloaliphatic and aromatic substituted aliphatic groups and specified N-acyl groups are derived from carboxylic and sulphonic acids.ALSO:Biocidal compositions contain a 4-substituted-aliphatic - 2,2 - dialiphatic - 1,2 - dihydroquino - line, or salts thereof, in which the 4-substituent is an alkoxy, thiocyano, mercapto, amino, hydroxyl, aryloxy, arylthio, thiazolethio, cyano, dithiocarbamyl, isothiuronium, acetoacetate or malonic ester group, in which one or more of the positions 5 to 8 of the dihydroquinoline nucleus can optionally contain as a substituent or halogen atom or an alkoxy, hydroxy, amino, nitro, aliphatic or aromatic group, and in which a halogen atom can optionally be present as a substituent in the 3-position, or a compound containing two 2,2-dialiphatic - 1,2 - dihydroquinol - 4 - yl - aliphatic radicals, or salt thereof, in which the linking groups are N,N-amino, N,N1-diamino, O,O1-glycol, S,S1-dithio, or S,S1-bis-(dithiocarbamate) and each dihydroquinoline nucleus can contain substituents in positions 5 to 8 and position 3 as stated above, in admixture with a diluent.  These compositions may be in the form of a liquid solution or emulsion or dispersion, when the diluent is an aqueous or organic solvent, or a solid, when the diluent is, for example, kieselguhr or talc. Specification 945,330 is referred to.