.beta.-phenoxyethylamines and their use for the preparation of dyestuffs
AssigneeBayer Aktiengesellschaft
InventorsKarl J. Herd, Wolfgang Harms
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Abstract
The preparation is described of compounds of the structure ##STR1## in which the substituents have the meanings indicated in the description. The compounds, which are in part new, are used as intermediate products for dyestuffs.
Claims3
A process for the preparation of a .beta.-phenoxyethylamine of the formula ##STR33## wherein Z is NH.sub.2 or NO.sub.2,
- M is H or an alkali metal cation, alkaline earth metal cation or ammonium cation,
- R is H or a C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl or C.sub.2 -C.sub.4 -alkynyl radical each of which is optionally substituted by OH, Cl, Br, CN, CO.sub.2 H, CO.sub.2 CH.sub.3, CO.sub.2 C.sub.2 H.sub.5, CONH.sub.2, CON(CH.sub.3).sub.2, SO.sub.3 H, OSO.sub.3 H or C.sub.1 -C.sub.4 -alkoxy, or a phenyl or benzyl radical each of which is optionally substituted by halogen, C.sub.1 -C.sub.4 -alkyl, CO.sub.2 H or SO.sub.3 H,
- R.sup.1 and R.sup.2 each independently is H, C.sub.1 -C.sub.4 -alkyl, phenyl or benzyl, or together they complete a cycloaliphatic ring,
- X is SO.sub.2 or CO and
- Y is SO.sub.3 M if X is SO.sub.2, and
- Y is H if X is CO,
- comprising
- a) cyclizing a 2-halogen-5-nitrobenzenesulphonamide or 2-halogeno-5-nitrobenzamide of the formula ##STR34## wherein Hal is Cl, Br or F, at 80.degree. to 110.degree. C. in the presence of a base to give a 5,1,2-benzoxathiazepin 1,1-dioxide (X.dbd.SO.sub.2) or a 1,4-benzoxazepin-5-one (X.dbd.CO), respectively, of the formula ##STR35## reducing the benzosultam or benzolactam to give an amino compound of the formula ##STR36## and hydrolyzing the amino compound with ring opening, or b) first hydrolyzing a benzosultam or benzolactam of the formula ##STR37## to give a compound of the formulae ##STR38## respectively, and then reducing the nitro group to an amino group.
A process for the preparation of the phenoxyethylamines according whereby benzosultams or benzolactams of the structure ##STR42## are first hydrolyzed to give compounds of the formulae ##STR43## respectively, and the nitro group is then reduced to the amino group.
Dependencies are inferred from the claim text.