Process for preparing carboxyalkyl-substituted hydroxylamine

Details Process for preparing carboxyalkyl-substituted hydroxylamine Process for preparing carboxyalkyl-substituted hydroxylamine

1990-11-09

1992-05-05

Shippen, Michael L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acids and salts thereof

558390, 558441, 562 11, 562 17, 562 43, 562105, 562443, 562444, 562448, 562553, 562561, 562567, 560 38, 560171, C07C22900

Patent

active

051109859

ABSTRACT:
A process for preparing a carboxyalkyl-substituted hydroxylamine represented by formula (I) ##STR1## where L represents an alkylene group; A represents a hydrogen atom, a sulfo group, a carboxy group, a phosphono group, a trialkylammonio group, a hydroxy group, an amino group, an acyl group, a carbamoyl group, a sulfamoyl group, an alkoxycarbonyl group, or a cyano group; and R.sub.1, R.sub.2, and R.sub.3, which may be the same or different, each represent a hydrogen atom, an alkyl group, or an aryl group; which comprises: reacting an .alpha.,.beta.-unsaturated carboxylic acid represented by formula (II) as an alkylating agent ##STR2## where R'.sub.1, R'.sub.2, and R'.sub.3, which may be the same or different, each represent the same group as defined for R.sub.1, R.sub.2, and R.sub.3, with a hydroxylamine of the formula HO--NH--R", where R" represents a hydrogen atom or an alkyl group which may be substituted with a sulfo group, a carboxy group, a phosphono group, a trialkylammonio group, a hydroxy group, an amino group, an acyl group, a carbamoyl group, a sulfamoyl group, an alkoxycarbonyl group, or a cyano group, in the presence of a solvent comprising: (a): (i) an organic polar solvent alone or (ii) a solvent mixture of water and an organic polar solvent when A is a sulfo group, a carboxy group, a phosphono group, or a trialkylammonio group; or (b): (i) water alone, (ii) an organic polar solvent alone, or (iii) a solvent mixture of water with an organic polar solvent when A is a hydrogen atom, a hydroxy group, an amino group, an acyl carbamoyl group, a sulfamoyl group, an alkoxy group, or a cyano group.

REFERENCES:
patent: 2195974 (1940-04-01), Reppe
patent: 3867445 (1975-02-01), Klemchuk
Posner, Berichte, 38, pp. 2316-2325 (1905).
"Houben-Weyl, Methoden der Organischen Chemie," Bd X/1, pp. 1115-1116 (1971).
Sandler, "Organic Functional Group Preparations," vol. III, pp. 321-327 (1972).

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