Patent GB-438122-A (GB)
Title: Improvements in the manufacture and production of quaternary ammonium compounds of derivatives of the anthracene series
IPC: C09B5/16
Filed: 1934-05-04
Abstract: Quaternary ammonium compounds of the anthracene series are obtained by treating anthrones bearing a nitrogen-containing six-membered ring attached in at least one periposition, with esters of strong acids, directly or in presence of diluents. According to examples: 4 - amino - 1 : 9 - anthrapyrimidine is combined with p-toluene sulphonic methyl ester in trichlorbenzene, 4-amino-1 : 9-anthraquinaldine is combined with dimethylsulphate in o-dichlorbenzene, 4-hydroxy-1 : 9-anthrapyrimidine is combined with dimethyl sulphate in trichlorbenzene, 2-brom-4-benzoylamino-1 : 9-anthrapyrimidine is combined with methyl iodide; 4 - amino - 1 : 9 - anthrapyrimidine is combined with phosphoric-normal-chlorethyl ester, the compound obtained by condensing 1-amino-4-benzoylamino-anthraquinone with acetoacetic ester is combined with dimethyl sulphate in trichlorbenzene, and anthrapyridone is combined with p-toluene sulphonic methyl ester, all to give the corresponding quaternary compounds, most of which are dyes.  A table giving the properties of the following compounds is also given: the quaternary compounds of p-toluene-sulphonic acid methyl ester with 1 : 9 - anthrapyrimidine and with 5 - amino-, 8-amino-, 2-amino-, 4-p-chlorbenzoylamino-, 5-p-toluidino-, 4-amino-C-phenyl-, 4-hydroxy-, 4 - methylamino-, Py - C - amino-, 4 - hydroxy-dichlor-, b -methyl-4-amino-, and Py-C-methyl-4-amino-1 : 9-anthrapyrimidines; the quaternary compounds of 4-amino-1 : 9-anthrapyrimidine with p-toluene-sulphonic acid ethyl ester, p-toluene-sulphonic acid chlorethyl ester, benzyl chloride, methyl bromide, methyl chloride, methyl iodide, ethyl chloride, dimethyl sulphate, and diethyl sulphate; the quaternary compounds of dimethyl sulphate with 4-p-chlorbenzoylamino-, dichlor-8-amino-, 2 : 4-diamino-, 4-amino-2-p-toluido, and 8-amino-1 : 9-anthrapyrimidines; the quaternary compound of 1 : 9 : 4 : 10-anthradipyrimidine with p-toluene-sulphonic acid methyl ester; and the quaternary compound of an amino-1 : 9-anthrapyrimidine (obtained from anthrapyrimidine by nitration and reduction) with p-toluene-sulphonic acid methyl ester. The dichlor-8-amino-1 : 9-anthrapyrimidine referred to above is obtainable by treating 8-amino-1 : 9-anthrapyrimidine with chlorine in the presence of chlorsulphonic acid and iodine at from 60 to 70 DEG  C.  Other pyrimidine derivatives specified include the chlor-, brom-, amino-, halogen-, acetylamino-, arylido-, dialkylamino, urea derivatives and diazo-salts of 1 : 9-anthrapyrimidines; quinaldine derivatives also specified include the amino-, benzoylamino-, brom-, and chlorquinaldines, and 1 : 9-anthraquinaldine itself; other heterocyclic derivatives of anthracene include the anthrapyrimidones, anthrapyrimidino-pyrimidones, and their mercapto, sulpho, nitro and alkyl derivatives.  Further specified esters of strong acids include o-toluene sulphonic esters, toluene sulphonic phenyl esters, octodecyl bromide, and chloride, vinyl chloride, and butyl bromide. Further specified solvents include chlorbenzenes, nitrobenzene, pyridine, benzyl ether or diphenyl.  Specification 28765/06, [Class 2], is referred to.