22185-75-7Relevant articles and documents
Synthesis and NMR-spectral characterization of N,N-dialkyl-3-nitroanilines, N,N-dialkyl-1,3-benzenediamines and their acyl derivatives
Katritzky, Alan R.,Rachwal, Bogumila,Rachwal, Stanislaw
, p. 337 - 345 (2007/10/02)
A recently discovered method for the synthesis of N,N-dialkyl-1,3-benzenediamines with two different alkyl groups is shown to be general.This is demonstrated by the synthesis of N-butyl-N-phenethyl-1,3-benzenediamine by the condensation of 3-nitroaniline with phenylacetaldehyde and benzotriazole, reduction of the adduct with sodium borohydride, acylation of the resulting N-phenethyl-3-nitroaniline with butyryl chloride, catalytic reduction of the nitro group by formic acid in the presence of triethylamine and palladium and finally reduction of the butyramide carbonyl group to the butyl substituent by lithium aluminium hydride.Several other routes were less efficient or failed completely.Classical methods for the synthesis of N,N-diethyl-1,3-benzenediamine were reexamined and improved.The recommended procedure involves alkylation of 3-nitroaniline with diethyl sulfate, trapping of N-ethyl-3-nitroaniline (by-product) by benzoylation, distillation of N,N-diethyl-3-nitro-aniline under reduced pressure and reduction of the nitro group by formic acid catalyzed by palladium.
Rubine disazo acid dyes for polyamides
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, (2008/06/13)
Dyes of the formula STR1 wherein B and D are each independently 1,4-phenylene or 1,4-naphthylene; M is hydrogen, lithium, sodium, potassium or ammonium; A1 is hydrogen, C1-4 alkoxy, C1-4 alkyl, trifluoromethyl, nitro, chloro, bromo, cyano, or hydroxy; B1 and B2 are each hydrogen, C1-3 alkoxy, C1-3 alkyl, chloro or bromo; D1 is hydrogen, C1-4 alkoxy, C1-4 alkyl, or chloro; D2 is hydrogen, C1-4 alkoxy, C1-4 alkyl, chloro, bromo, fluoro, or acylamino, acyl being C1-5 alkanoyl, C1-5 alkylsulfonyl, benzoyl or benzenesulfonyl, each acyl unsubstituted or substituted with 1 to 3 of C1-2 alkyl, C1-2 alkoxy, chloro, bromo, cyano, or hydroxy; and R1 and R2 are each C1-6 alkyl, C1-6 chloro or bromoalkyl, C2-6 hydroxy- or dihydroxyalkyl, C2-6 alkoxyalkyl, C1-6 cyanoalkyl, or phenyl-C1-2 alkyl (phenyl unsubstituted or substituted with 1 to 3 of C1-2 alkyl, C1-2 alkoxy, chloro, bromo, cyano or hydroxy) are useful in dyeing natural and synthetic polyamide fibers in deep and level shades of red to blue.