1- Anilino-2-methoxy

Methan Anilino-methoxy- E14a/2, 249 (R— NH2(CH20,/Na0R)... 

Quinoline, amino-2-hydroxy-4-methyl-azo pigments from, 1, 334 Quinoline, 8-amino-6-methoxy-as antimalarial, 2, 517 Quinoline, 4-amino-2-methyl-protonation, 2, 341 Quinoline, anilino-3-substituted... 

Anilino-3-(4-dimethylamino-anilino)- 2-Anilino-3-(4-methoxy-anilino)-buten-(2)-saure-anilid 2-Anilino-3-(4-methoxy-anilino)-buten-(2)-saure-2,5-dimethyl-anilid... 

Preparation of 2 -Anilino-6 -diethylamino-3 -methylfluoran (77d). To a solution of 2-(4-diethylamino-2-hydroxybenzoyl)benzoic acid (0.1 mol) in 98% sulfuric acid (1 50 g) was added 4-methoxy-2-methyldiphenylamine (0.1 mol) in limited amounts, while the temperature was maintained to not rise above 30 °C. The resulting mixture was stirred at room temperature for 20 h, and poured into ice water (1000 ml). The precipitate was filtered off, washed with water, and then refluxed with a mixture of toluene (400 ml) and 20% aqueous sodium hydroxide (150 g) for 1 h. The toluene layer was separated, washed with hot water, and concentrated to leave ca. 100ml of toluene. The residue was then refluxed with methanol (100 ml) for 1 h. After being cooled, the precipitate is filtered off, washed with methanol, and dried to give 2 -anilino-6 -diethylamino-3 -methylfluoran in 90% yield as an off-white powder, mp 197-198 °C. 

Preparation of 2 -Anilino-6 - [N- (3-bromopropyl) -N-ethylaminoJ-3 -methylfluoran (89). To a mixture of 2 -anilino-6 -[/V-ethyl-Af-( 3-methoxy-propyl)amino]-3 -methylfluoran (0.1 mol) and 48% hydrobromic acid (150 ml) was added dropwise concentrated sulfuric acid (20 ml) with vigorous stirring. Then, the resulting mixture was stirred at 110-115 °C for 1 h, poured into ice water (1000ml), and made alkaline by aqueous sodium hydroxide. The pale violet precipitate was filtered off, and recrystallized from ethyl acetate-isopropanol to give 2 -anilino-6 -[/V-(3-bromopropyl)-,V-ethylamino]-3 -methylfluoran in 96% yield, mp 160-162 °C. 

The influence of the nature of the substituent at position 4. In order to determine the influence of substituents at position 4 on the Sn(ANRORC) process in the aminodehalogenation, the amide-induced amination was studied with 6-chloropyrimidines containing different substituents at position 4, i.e., the 4-Ubutyl-, 4-methoxy-, 4-piperidino-, 4-anilino-, and 4-methyl-groups (79RTC5). The results are summarized in Table ILl. 

Furukawa et al. reported the total synthesis of murrayaquinone A (107) by a palladium(II)-mediated oxidative cyclization of the corresponding 2-arylamino-5-methyl-l,4-benzoquinones. 2-Anilino-5-methyl-l,4-benzoquinone (842) was prepared starting from 2-methyl-l,4-benzoquinone 841 and aniline 839, along with the regio-isomeric 2-anilino-6-methyl-l,4-benzoquinone (844). The oxidative cyclization of 2-anilino-5-methyl-l,4-benzoquinone (842) with stoichiometric amounts of palla-dium(ll) acetate provided murrayaquinone A (107) in 64% yield. This method was also applied to the synthesis of 7-methoxy-3-methylcarbazole-l,4-quinone (113) starting from 3-methoxyaniline (840) (623). Seven years later, Chowdhury et al. reported the isolation of 7-methoxy-3-methylcarbazole-l,4-quinone (113) from the stem bark of Murraya koenigii and named it koeniginequinone A (113) (49) (Scheme 5.101). 

Formyl-3-methyl-2-( 2-methoxy-4-nitro-anilino)-2,3-dihydro-indazol wenig (bei pH = 6 42%)... 

OCHj 4-Anilino-2-carboxy-3,6-dihydroxy-4 -meth-oxy-... 75 170 4-A mlino-2,5-dihydroxy-4 -methoxy-... 94 190... 

OCH3 4-CH3 2-Carboxy-3,6-dihydroxy-4- (2-methoxy-aniltno) -4 -methyl-... 89 184 2,5-Dihydroxy-4- (4-meth-oxy-anilino)-4 -methyl-... 90 209... 

Benzylische Acyloxy-Gruppen wie z.B. in 4,7-Diacetoxy-6-methoxy-2-methyl-l,2,3,4-te-trahydro-isochinolin werden bei der Reaktion mit primaren Aminen unter milden Bedin-gungen durch eine Alkylamino- Oder Arylamino-Gruppe ersetzt gleichzeitig wird die zwei-te Acetoxy-Gruppe im Molekul hydrolysiert, so daB man mit Ethylamin bzw. Anilin 4-Ethylamino-7-hydroxy-6-methoxy-2-methyl- (82%) bzw. 4-Anilino-7-hydroxy-6-meth-oxy-2-methyl-l,2,3,4-tetrahydro-isochinolin (66%) erhalt1. 

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