Diethyl toluidine

A comparative spectroscopic and photochemical study of Brilliant Green leu-conitrile (BGCN) and A/,iV-diethyl-/>-toluidine (DET) at room and low temperature and in polar and nonpolar solvents was conducted by Geiger et al. [15]. At 77 K the spectroscopic and photochemical properties of BGCN were solvent independent. However, at room temperature the quantum yield of ionization was 0.8-0.9 in ethanol and 25% lower in both acetonitrile and 4% water/ethanol. 

The precursor aryl-malonamide 21 is prepared in a three-step procedure from 2,6-diethyl-toluidine. A technically feasible cross<oupling reaction has been developed for the synthesis of aryl malononitrile 20 starting from benzene derivative 19 and malononitrile. The optimized procedure with PdQ2/tricyclo-hexylphosphine and sodium tert-butoxide as base in refluxing xylene [81] was improved even further using palladium dichloride/triphenylphosphine as catalyst and sodium hydroxide as base in l-methyl-2-pyrrolidone at 125-130 °C [82]. The aryl-malononitrile 20 is hydrolyzed to the aryl-malonamide 21 in cone, sulphuric acid. 

Reaction of o-toluidine with chloral hydrate in presence of hydroxylamine hydrochloride and subsequent treatment with H2SO4 gave the isatin derivative 337. Bromination of 337 followed by reaction with sodium diethyl malonate gave 338. Catalytic reduction with Pd/C gave the oxoindole derivative 339 that upon hydrolysis with aqueous NaOH followed by... 

Dipping solution Dissolve 2.5 ml o-toluidine in a mixture of 45 ml diethyl ether and 5 ml glacial acetic acid [7]. 

Heating pyridine-2,3-dicarboxylic acid anhydride with l-ethyl-2-methylindole has been claimed to yield solely the pyridine-2-carboxylic acid, albeit in low yield. This then clearly reacts with Af,A/-diethyl-3-toluidine in acetic anhydride to give the 7-azaphthalide. This is surprising in view of a later report70 in which a one-pot process has been described. Heating pyridine-2,3-dicarboxylic anhydride, prepared in situ, with the indole and subsequent reaction with 3-/V,/V-diethylamino-phenetol under identical conditions to those used in Scheme 8 (but without intermediate isolations) produced a 20 1 mixture of the 4- and 7-azaisomers 16 and 17. It appears that in the previous report the major intermediate isomer, the pyridine-3-carboxylic acid, has not been isolated. 

When diethyl phenyl(phenylamino)methylenemalonate (4) was heated in the presence of p-toluidine at 150°C, the N-(4-methylphenyl)amide of 2-phenylquinoline-3-carboxylate (7, R = H) was obtained (36JCS428). 

Phenylamino)phenylmethylenemalono-(di-p-toluidine) (1556) was prepared when diethyl (phenylamino)phenylmethylenemalonate (4) was heated at 110-120°C in the presence of p-toluidine (36JCS428). 

Knoevenagel condensation of the corresponding 3-methylfuran-2-carbaldehyde 379 and 3-methybenzo[4]furan-2-carbaldehyde 382 with diethyl malonate followed by bromination with iV-bromosuccinimide (NBS) in the presence of dibenzoyl peroxide afforded bromides 380 and 383, respectively. Treatment of 380 and 383 with benzylamine, isopropylamine, /-butylamine 3-hydroxypropylamine, aniline and -toluidine in ethanol yielded furo[2,3-c]pyrroles 381 and benzo[4,5]furo[2,3-c]pyrroles 384, respectively (Scheme 41). The yields of furopyrroles 381 are only moderate (16-46%), because these compounds are highly sensitive to acid, and partially polymerized upon silica... 

For application temperatures below 10°C or for acceleration of cure rates at room temperature, nonredox systems such as benzoyl peroxide initiated by tertiary amines such as dimethylaniline (DMA) have been applied widely. Even more efficient cures can be achieved using dimethyl- )-toluidine (DMPT), whereas moderated cures can be achieved with diethyl aniline (DEA). 

Representatives of this class are also suitable for dyeing cellulose triacetate. However, sufficient lightfastness is not obtained on synthetic polyamides [10], Other industrially important 2,6-dicyanoazo dyes are obtained by using diethyl- m -toluidine and 3-diethylaminophenylmethansulfonamide [52603-47-1] as coupling components (see 23 and 24, respectively). 

The Friedel-Crafts acylation of acetanilide with chloroacetyl chloride yields l-acetamido-4-chloroacetylbenzene. The trimethylammonium group is introduced by reaction with trimethylamine, followed by hydrolysis of the acetamide group. This diazo component is a constituent of numerous yellow, orange, and red cationic azo dyes. Using diethyl- m-toluidine as the coupling component, the lightfast red dye 35 [67905-12-8] is obtained [99],... 

Fig. 5. PMR spectra (60 MHz) of the methylene quartet of iV.AT-diethyl-p-toluidine (0.02-M) in an acetonitriIe-d3 solution containing 0.02-M decafluorobenzophenone in the dark (left) and during UV irradiation (center). The difference spectrum (light minus dark right) seems to show emission signals, an artefact of the mathematical operation. The artefactual enhancement factor is near-1 [177]...

Thiophosgene (1.15 g, 0.01 mol) in chloroform (40 ml) was slowly treated at room temperature with sodium l,4-methano-l,2,3,4-tetrahydro-6-naphthoxide (1.82 g, 0.01 mol). After 30 minutes, N-methyl-m-toluidine (2.42 g, 0.02 mol) in chloroform (40 ml) was added dropwise to the solution so obtained at room temperature. The reaction mixture was stirred for 48 hours at room temperature and then refluxed for 2 hours. The solvent was evaporated, and the residue redissolved in water and extracted repeatedly with diethyl ether. The organic phase was dried (Na2S04) and evaporated to... 

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