N-Butyl-4-methyl

The corresponding 4-aminoquinolines were obtained in 42-98% yield. In the synthesis of 4-methyl-2-quinolinamine which was prepared in 49% yield, using N,N-dimethylcyclohexylamine as the tertiary amine component of the reaction mixture, N-mono-and N,N-dimethylated quinolinamines could also be isolated in 16% and 3% yield, respectively. If tributylamine was used as the tertiary amine component, the yield of 4-methyl-2-quinolinamine increased to 68% and N-butyl-4-methyl-2-quinolinamine was only formed in 6% yield. In the latter reaction pure 4-methyl-2-quinolinamine was easily obtained by recrystallizing the raw material. 

Dehydrogenation of cernuine over Pd-charcoal yielded 2-n-butyl-4-methyl-6-w-pentylpyridine in 10% yield, identified by comparison with a synthetic specimen. This product accounted for all but one of the 16 carbon atoms of cernuine. The biogenetic scheme proposed by Conroy (27) has been unusually successful in accommodating the Lycopodium alkaloids of known structure and when applied to this problem it led to structures CXLVI-A and CXLVI-B for cernuine and lycocernuine, respectively. The numbering system, adopted by Ayer et al. and shown in formula CXLVI, indicates how the two polyacetate units may be linked. Structures CXLVI-A and B are in accord with the spectral data of cernuine, lycocernuine, and their derivatives discussed above. The formation of 4-methyl-2-7i-butyl-6-m-pentylpyridine in dehydrogenation may be readily accounted for. Moreover, the two structures accounted for the major peaks found in the mass spectra of the two alkaloids. 

N-butyl-4-methyl-pyridinium tetrafluoroborate hydrophilic RTIL... 

Denmark and coworkers have found that methylaluminum bis (2,6-di-tert-butyl-4-methyl-phenoxide) (MAD) or methylaluminum bis(2,6-diphenylphenoxide) (MAPh) is effective as the Lewis acid promoter for cycloaddition of 2,2-disubstituted 1-nitroalkenes (Eq. 8.100).158 Other Lewis acids such as SnCl4, TiCl4, and TiCl2(Oi-Pr)2 fail to promote the cycloaddition of 2,2-disubstituted 1-nitroalkenes. The products are converted into 3,3-disubstituted pyrrolidines via hydrogenolysis.158 Reductive cleavage of N-0 bonds produces oxime hemiacetals, which are further reduced to amido aldehydes and finally to pyrrolidines. This reaction provides a useful synthetic method for pyrrolidines, which is discussed later. 

This is a general method for making N-alkylallenimines, and the following ones have been made in this way N-methyl-,6 N-propyl-,6 N-isopropyl-,4 N-butyl-,4 N-hexyl-,e and N-(3,5,5-tri-methylhexyl)-.4 N-Z-Butylallenimine6 and l-(l-allenimino)-2-hydroxy-3-butene 7 have also been prepared by this method, but with sodium amide/2-bromoallylamine mole ratios of 1.75 and 2.1, respectively. This method has been used for the preparation of pure N-alkylpropargylamines from 2-chloroallylaminesA7 The optimum sodium amide/2-chloroallylamine ratio for the preparation of N-alkylpropargylamines is 2.1. 

Name 2-Methyl-4 -n-butyl-4-(4-n-butoxybenzoyloxy) azobenzene Structure ... 

Asymmetric amino-acid synthesis.1 The (S)-l-f-butyl 4-methyl N-benzyloxy-carbonylaspartate (1), prepared in 80% yield from the 4-methyl ester of aspartic acid, undergoes diastereoselective alkylation at the -carbon (LDA or lithium hexa-... 

The saponification of the 3-n-butyl-6-methyl-3,4-dihydro-l,2-pyran was accomplished by heating for 0.5 h in a mixture with acetic acid. The 1-methyl-... 

Synthesis of 2-n-butyl-4-spirocyclopentane-l-[(2 -(tetrazol-5-yl)biphenyl-4-yl)-methyl]-2-imidazolin-5-one... 

Bromomethyl-2-cyanobiphenyl (4.6 g) was alkylated onto 2-n-butyl-4-chloro-5-(hydroxymethyl)-imidazole. For separation of the product was used a flash chromatography in 1 1 hexane/ethyl acetate over silica gel. The regioisomeric products yielded 2.53 g of the faster eluting isomer. Recrystallization from acetonitrile yielded 1.57 g of analytically pure 2-n-butyl-4-chloro-l-[2,-cyanobiphenyl-4-yl)methyl]-5-(hydroxymethyl)-imidazole, melting point 153.5 -155.5°C. 

Marcus treatment does not exclude a radical pathway in lithium dialkyl-amide reduction of benzophenone. It does, however, seem to be excluded (Newcomb and Burchill 1984a,b) by observations on the reductions of benzophenone by N-lithio-N-butyl-5-methyl-l-hex-4-enamine in THF containing HMPA. Benzophenone is reduced to diphenylmethanol in good yield, and the amine yields a mixture of the acyclic imines no cyclic amines, expected from radical cyclization of a putative aminyl radical, were detected. An alternative scheme (17) shown for the lithium diethylamide reduction, accounts for rapid formation of diphenylmethoxide, and for formation of benzophenone ketyl under these conditions. Its key features are retention of the fast hydride transfer, presumably via the six-centre cyclic array, for the formation of diphenylmethoxide (Kowaski et al., 1978) and the slow deprotonation of lithium benzhydrolate to a dianion which disproportion-ates rapidly with benzophenone yielding the ketyl. The mechanism demands that rates for ketyl formation are twice that for deprotonation of the lithium diphenylmethoxide, and, within experimental uncertainty, this is the case. 

Experiments have been carried out with the rotating cryostat to study the reaction of 2,6-di-t-butyl-4-methyl phenol (lonol) with n-heptyl and n-heptylperoxy radicals. When lonol was deposited on n-heptyl radicals the e.s.r. spectrum showed that some reaction had occurred at 77°K. When the deposit was warmed slowly the spectrum of the residual n-heptyl radicals disappeared and was replaced by that of the substituted phenoxy-radical, (4), formed by loss of the hydroxyl hydrogen. 

Sulfoxid (2-Dimethylhydrazono-butyl)-(4-methyl-phenyl)- E21b, 1753 [R2N-N = C(C2H5)-CH3 + LiNR2/Ar — SO —OR]... 

SYNS 7-(BENZYLOXY)-6-N-BUTYL-l,4-DIHYDRO-4-OXO-3-QUINOLINECARBOXYLIC ACID METHYL ESTER 7-(BENZYLOXY)-6-N-BUTYL-4-HYDROXY-3-QUINOLINECARBOXYLIC ACID METHYL 3-METHOXYCARBONYD6-N-BUTYD7-BENZYLOXY-4-OXOQUINOLINE STATYL... 

BENZYLOXY)-6-N-BUTYL-4-HAT)ROXY-3-QUINOLINECARBOXYLIC ACID METHYL see NCN600... 

Related Reagents. l-Benzoyl-2-r-butyl-3,5-dimethyl-4-imi-dazolidinone (2S,4S)-3-Benzoyl-2-/-butyl-4-methyl-1,3-oxazo-lidin-5-one N-Benzyloxycarbonyl-t-serine p-Lactone N-r-Buto-xycarbonyl-N-methylaminomethyllithium (R)-2-r-Butyl-6-methyl-4H-l, 3-dioxin-4-one N, N-Diethylaminoacetonitrile Ethyl N-(Diphenylmethylene)glycinate Ethyl Isocyanoacetate Methyl ot-Phenylglycinate... 

Also, antioxidants were found to decrease the aging rate of natural rubber. Among the antioxidants more frequently used are N-phenyl-p-naphthylamine, 2,6-di-tert-butyl-4-methyl-1-hydroxybenzene (BHT), N-isopropyl-N -phenyl-p-phenylenediamine, N-(1,3-dimethylbutyl)-N -p-phenylenediamine, and poly-(2,2,4-trimethyl-1,2-dihydroquinoline). 

Methylpiperazine (70) gave butyl 4-methyl-l-piperazinecarboxylate (69) (BuCl, BU2NSO4H, K2CO3, n-CvHjg, reflux, 4 h 15%, note the incoipora-tion of CO2) but only l-butyl-4-methyIpiperazine (71) in the absence of a phase-transfer catalyst (BuBr, K2CO3, MeCN, reflux, —2.5 h 86%). ... 

Exceedingly bulky aluminum reagent aluminum tris(2,6-di-tert-butyl-4-methyl-phenoxide) (ATD) [113] was superior to ATPH or MAD as a carbonyl protector in ynones [114]. Initial complexation of 3-octyn-2-one (115) in toluene with ATD and subsequent addition of a hexane solution of n-BuLi at -78 °C generated 1,4-adduct 116 in 92% yield with a small amount of the 1,2-adduct (Scheme 6.90). 

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