2- Anilino-1-hydroxy

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... 

Auf analoge Weise erhalt man aus N-Anilino-phthalimid in schwach saurer Losung2-Anilino-3-hydroxy-1-oxo-2,3-dihydro-isoindol (79% d.Th. F 1480)1 ... 

Preparation of 6 -[4-(4-Anilinoanilino)anilino]-2 -chloro-3 -methylflu-oran (81a). To concentrated sulfuric acid (10 g) was added 2-(5-chloro-2-hydroxy-4-methylbenzoyl)benzoic acid (3.4 mmol) followed by 4-anilino-4 -(3-methoxyanilino)diphenylamine (2.6 mmol). The mixture was stirred at room temperature for 24h, and poured into ice water (100ml). The precipitate was filtered off, washed with water, and then refluxed with a mixture of toluene (150 ml) and sodium hydroxide (20 g) dissolved in water (150ml) for 1 h. The toluene layer was separated, washed with hot water, and concentrated. The residue was then column chromatographed on silica gel to give 6 -[4-(4-anilinoanilino)anilino]-2 -chloro-3 -methylfluoran in 43% yield as a grayish white powder, mp 202-203 °C. 

DAST-type FBAs may contain by-products (such as 11.13) derived from hydrolysis of one or more of the chloro substituents in cyanuric chloride (11.10). One such troublesome byproduct is 2,4-bis(anilino)-6-hydroxy-s-triazine (11.62). Not only is this compound environmentally undesirable, it may also interact with certain bleaching agents and its presence can lead to the development of unpleasant odours on storage of a detergent... 

Alkyl-3-hydroxy-4-pyridinones can be converted into analogues containing, e.g., anilino-, phenylthio-, or 2-hydroxyethylthio-substitu-ents by silver(I) oxidation (Ag20 in ethanol) followed by Michael addition (71). In aminomethylation of 3-hydroxy-4- and -2-pyridinones under Mannich conditions the position of substitution can be tailored, by reaction conditions to position C4 or C6, or by converting the OH into OMe, which directs substitution to C5 (72). 

Ethyl 2-ethylthio-4-chloro-5-pyrimidinecarboxylate (XXIIa), as well as the corresponding4-hydroxy-(XXIIb) and 4-amino-(XXIIIa) derivatives, possess-anti-cytogenic activity on Neurospora crassa [223, 224]. Compounds (XXIIIa, b and c) were found to inhibit the conversion of orotic acid to the uridine nucleotides [202]. Ethyl 2-methylthio-4-(halo-substituted anilino)-5-pyrimidinecarboxylates (XXIV), particularly the o-bromo- and the o-chloro- derivatives, substantially inhibit the growth of five experimental mouse tumours (Krebs-2 ascites carcinoma, Ehrlich carcinoma clone 2, leukaemia L-1210, carcinoma 755 and lymphocytic neoplasm P-288) [225]. Compounds of this type are usually prepared by the base catalysed condensation of ethoxymethylenemalonic esters or related derivatives with urea, thiourea, guanidine, or substituted amidine-type analogues [212, 225-237]. 

Thermolyse von N-(2-Amino-anilino)-harnstoffen605 odcr von -semicarbaziden592 liefert nur das unsub-stituierte 2-Hydroxy-benzimidazol (90%). 

Die Cyclodehydratisierung von l-(2-Hydroxy-anilino)-phthalazinen gelingt elektrophil mit Polyphosphorsaure und liefert kondensierte Benzimidazole mit anti-inflammatorischer (entziin-dungshemmender) Wirkung116 ... 

HO -b -Oci Benzol/Aceton 6 h Riickfl. 2-(4-Chlor-anilino)-5-( 2-hydroxy-phenyl) -... 91 248-249 439... 

Cl 4-Anilino-2-carboxy-4 -chlor-3,6-dihydroxy-... 86 203 4- Anilino-4 -chlor-2,5-di-hydroxy-. .. 89 203... 

CI 4-CH3 2-Carboxy-4-( 4-chlor-anilino) -3,6-dihydroxy-4 -methyl-... 78 180 4-(4-Chlor-anilino)-2,5-di-hydroxy-4 -methyl-. .. 98 198... 

Ethoxy-anilino)-ethoxy]-ethanol1 Ein Gcmisch von 27,4 g (0,2 mol) 4-Ethoxy-anilin, 190 g (1,78 mol) Bis-[2-hydroxy-ethyl]-ether und 20 g Raney-Nickel wird im Stickstoff-Strom untcr Riihren 12 h auf 150° crhitzt. AnschlieBend wird filtriert, iibeTschussigcr Bis-[2-hydroxy-ethyl]-cthcr (Solvens) abgczogen undder Ruckstand i.Vak. dcstilliert Ausbeule 25,8 g (57%) Sdp. 155 160°/0,1 Torr (13,3 Pa) Schmp. 49 51°. 

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. 

Verwcndet man in der 3. Stufe des angegebenen Formelschemas einen Aldehyd anstelle des Alkyl-bromids, so erhalt man einen jS-Amino-alkohol, z. B. durch Metallierung von (2-Anilino-ethyl)-quecksilber-bromid (aus Ethen durch Aminomercurierung) mit Phenyllithium und anschlicBende Umsetzung mit 2-Methyl-propanal l-Anilino-3-hydroxy-4-methyl-pentan (70%)2. 

QfN"CH3 + HO- Y0 20% 48 h 3-Hydroxy-2-hydrOXymethyl-l-methyl-4-( N-methyl-anilino)-1,2,3,4- tetrahydro-chinolin 45 7... 

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