公开(公告)号：DE19738864A1

公开(公告)日：1999-03-11

申请号：DE19738864

申请日：1997-09-05

Applicant: BASF AG

Inventor： KLINTZ RALF DR ,  GOETZ NORBERT DR ,  KEIL MICHAEL DR ,  HEILIG MANFRED DR ,  WINGERT HORST DR ,  VOGELBACHER UWE JOSEF DR ,  WAHL JOSEF ,  WITTERICH FRANK DR

IPC: C07C259/04 ,  C07D231/20 ,  C07C239/10

Abstract: N-acylated (hetero)aromatic hydroxylamine derivatives are prepared by hydrogenation of the corresponding nitro compound in the presence of an inert, aprotic solvent and an aliphatic amine. N-acylated(hetero)aromatic hydroxylamine derivatives of formula (1) are prepared by hydrogenation of a (hetero)aromatic nitro compound of formula (2) in the presence of a hydrogenation catalyst. The hydrogenation is carried out in a mixture at an inert, aprotic solvent and an aliphatic amine followed by removal of the amine by distillation or extraction to yield a crude hydroxylamine without intermediate isolation that is N-acylated to form the compound of formula (3) and optionally by o-alkylation of form the compound of formula (4), R = 1-4 C alkoxycarbonyl, alkylcarbonyl, alkylaminocarbonyl, di(1-4 C alkyl)aminocarbonyl; R = H or 1-6 C alkyl; R = H, halogen, cyano, 1-4 C alkyl, 1-4 C haloalkyl, 1-4 C alkoxy, 1-4 C alkyl-CRd=N-O-1-4 C alkyl, 1-4 C alkoxycarbonyl, -CH2O-N=C(Ra)-C(Rb)=N-O-Rc or A or B; A = -O-, -CH2-, -O-CH2, CH2O-, -CH2OCO-, -CH=CH-, -CH=N-O-, -CH2-O-N=C (Ra) or a single bond; B = phenyl, napthyl, pyridinyl, pyrazinyl, pyrinidinyl, pyridazinyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,4-triazolyl; 1,2,3 triazolyl, furanyl, thienyl, pyrrolyl or 3-7 C cycloalkyl, optionally substituted with 1-3 Ri groups. Ri = H, halogen, cyano, 1-4 C alkyl, 1-4 C haloalkyl, 1-4 C alkoxy, 1-4 C alkyl-CR =N-O-1-4 C alkyl, 1-4 C alkoxycarbonyl, 1-4 C alkylaminocarbonyl, 1-4 C dialkylaminocarbonyl, 1-4 C alkylcarbonylamino, 1-4 C alkylcarbonyl-1; 4-alkylamino or phenyl, optionally substituted by halogen or 1-4 C alkyl Rd = H, 1-4 C alkyl, 2-4 C alkoxy or 2-4 C alkenyl; Ra, Rc = H, halogen, cyano, 1-4 C alkyl, 1-4 C alkoxy, 1-4 C alkylthio, cyclopropyl or trifluoromethyl; Rb = 1-4 C alkyl, 2-4 C alkenyl, 3-6 C cycloalkyl, phenyl, hetaryl or heterocyclyl R = halogen, 1-4 C alkyl, 1-4 C haloalkyl or 1-4 C alkoxycarbonyl X = N or CH; n = 0, 1, 2 or 3.