GB730243A - - Google Patents

Abstract

730,243. Diphenytpyridytmethanes. THOMAE GES., DR., K. March 17, 1953 [March 17, 1952; Jan. 12, 1953; Jan. 12, 1953; Jan. 12, 1953], No. 7365/53. Class 2 (3). The invention comprises compounds of the formula. where Pyr is a pyridine residue (which may contain alkyl substituents), Y is hydroxy, alkoxy or acyloxy, R<SP>1</SP> is hydrogen, alkyl, aryl and aralkyl, and R 1 -R 4 are hydrogen, alkyl, aryl, aralkyl, hydroxy, alkoxy or acyloxy. These are made by (1) condensing pyridine aldehydes or ketones with 2 mols. of the appropriate phenol; if Y is alkoxy or acyloxy the OH groups may be etherified or esterified before, during or after the condensation; (2) as in (1) using acetals or bisulphite compounds of the aldehydes or ketones; (3) condensing pyridine aldehydes or ketones with 2 mols. of aromatic amine and replacing the amino groups by hydroxyl via the diazonium salts. The condensation is effected in the presence of a dehydrating agent such as sulphuric, phosphoric or hydrochloric acid, zinc chloride, stannic chloride, a phosphorus halide, aluminium chloride or boron trifluoride, and preferably an inert solvent such as benzene, toluene or xylene. An esterifying agent such as acetic anhydride may be present simultaneously. Condensation with the phenols can be carried out at, below, or slightly above room temperature. The amines in method (3) are condensed at 100-126‹ C. The products are laxatives and disinfectants. In the examples, the following are made by direct condensation: di-(phydroxyphenyl) - (2 - pyridyl) - methane, di - (4 - hydroxy - 2 - methylphenyl) - (2 - pyridyl) - methane, di - (4 - hydroxy - 3 - methylphenyl) - (2 - pyridyl) - methane, di - (4 - hydroxy - 3 - isopropyl - 6 - methylphenyl) - (2 - pyridyl) - methane, di - (4 - hydroxy - 3 - phenylphenyl) - (2 - pyridyl) - methane, di - (4 - hydroxy - 3 - benzylphenyl) - (2 - pyridyl) - methane, di - (p - hydroxyphenyl) - (3 - pyridyl) - methane, 1 : 1 - di - (p - hydroxyphenyl) - 1 - (3 - pyridyl) - ethane, di - (p - methoxyphenyl) - (2 - pyridyl) - methane, di - (p - hydroxyphenyl) - (2 - pyridyl)- phenyl - methane, di - (4 - hydroxy - 3 - methoxyphenyl) - (2 - pyridyl) - methane, di - (p - hydroxyphenyl) - (4 - pyridyl) - methane, 1: 1 - di - (p - hydroxyphenyl) - 1 - (6 - methyl - 3 - pyridyl) - ethane, di - (p - hydroxyphenyl) - (6 - methyl - 2 - pyridyl) - methane, 1: 1 - di - (p - hydroxyphenyl) - 1 - (2 - pyridyl) - ethane, di - (p - aminophenyl) - (2 - pyridyl) - methane (converted to dihydroxy compound), and di-(paminophenyl) - (6 - methyl - 2 - pyridyl) - methane (converted to dihydroxy compound). 'In a further example di-(p-hydroxyphenyl)-(2- pyridyl)-methane is di-acylated with acetic anhydride and sodium acetate. It is stated that m-toluidine and o-anisidine also may be used for method (3).