4-methoxy-phenyl hydrazine

However, in the reaction of cyclohexanone, benzylisonitrile, 4-methoxy-phenyl-hydrazine and acetic acid a dihydro-cinnoline was formed by a novel MCR (Scheme 10.4). 

Dihydrocinnoline derivative 235 could be synthesized from the [2-(2,2-dimethoxyethyl)phenyl]hydrazine 234 via acid-catalyzed cyclization in dioxane. When methanol was used as solvent, a 3-methoxy-l,2,3,4-tetrahydrocinno-line 236 was formed (Scheme 62) <1995LA1303>. 

Hydrazin (2,6-Dichlor-4-trifluor-methoxy-phenyl)- E16a, 657 (Ar-Nf-Red.)... 

Butyloxy-benzyl)- E16a, 432 (Hydrazin-Alkyl.) [3-(4-Methoxy-phenyl)-l -methyl-propyl]- E16a, 446 (Hydrazon-Red.)... 

Geht man direkt von 1,3-Dinitro-alkanen aus, werden mit Hydrazin-Hydrat und 1,3-Dinitro-2-phenyl-butan oder 2,4-Dinitro-3-(4-methoxy-phenyl)-pentan 3(5)-Methyl-4-phenyl- (56% Schmp. 140-142°) bzw. 3,5-Dimelhyl-4-(4-methoxy-phenyl)-IH-pyrazol (68% Schmp. 153-155°) erhalten. 1-Nitro-l-alkene cyclisieren thermisch in Dimethylformamid mit D-Ga-lactose-phenylhydrazon2138 ... 

Methoxy-phenyl)-3(5)-phenyl)-1 H-pyrazol 2,6 g(10,2 mmol) 2-(4-Methoxy-phenyl)-3-oxo-3-phenyl-propanal werden in 20 ml Ethanol mit 0,6 ml (14,6 mmol) 78% Hydrazin-Hydrat 45 min. am RiickfluB erhitzt. Nach dem Verdiinnen mit Wasser wird mit Diethylether ausgeschiittelt, die organ. Phase mit Mare eingeengt, Der Riickstand wird aus... 

Analog wird 4-Formyl-7-methoxy-benzofurazanoxid mit Hydroxylamin-Hydrochlorid, O-Me-thyl-hydroxylamin-Hydrochlorid bzw. 1.1-Dimethyl- oder Phenyl-hydrazin zu Oximen bzw. Hydrazonenumgcsetzt, dieisoliert werden undbeimErhitzen2-Amino - bzw. 2-Hydroxy-2H-indazole liefern z.B. ... 

Wahrend 3-Methyl-3-(4-methoxy-phenyl)-butanon-(2)-azin fiber Platin(IV)-oxid in Essigsaure zum primaren Amin (83% d.Th.) hydriert wird, kann durch Zugabe von Essig-saure-athylester die Hydrogenolyse vermieden werden, und man erhalt Bis-[3-methyl-3-(4-methoxy-phenyl)-butyi -hydrazin °. Im 3-Methyl-3-(4-nitro-phenyl)-butanon-(2)-azin wird mit Palladium/Kohle (10%) bei 3,5 bar in Tetrahydrofuran zunachst die Nitro-... 

Chloro-5,6-diphenyl-as-triazine readily undergoes methoxy-de-chlorination at 25° (< 12 hr) with methanolic methoxide and at 65° (4.5 hr) in non-basified methanol. The chloro group is also displaced by hydrazine (80°, 1 hr), ammonia (140°, 6 hr), and phenyl-magnesium bromide (70°, 12 hr), the latter forming the triphenyl compound 315.3-Chloro-6-phenyl-as-triazine is unstable to cold water or alkali and to hot alcohol or aqueous potassium carbonate. ... 

The methoxy group is replaced in the reaction of 3-methoxy-5-phenyl-1,2,4-triazine 1-oxide 46 with ammonia, resulting in 3-amino-5-phenyl-1,2,4-triazine 1-oxide 47. The treatment of 3-methoxy-1,2,4-triazine 1-oxide 20 with hydrazine leads to 3-hydrazino-1,2,4-triazine 1-oxide 48 (71JOC787). 

Iwakawa et al. studied the reaction of 3-acetonyl-5-cyano-l,2,4-thiadiazole 72 with a series of 4-substituted phenylhydrazine hydrochlorides. When electron-donating substituents were used (e.g., methyl and methoxy) in the phenyl ring of the hydrazine, the reaction proceeded via a Fischer-indole mechanism to give indoles 73 as the sole product. In contrast, reaction of 72 with phenylhydrazine and 4-chlorophenylhydrazine gave only small amounts of indole 72, but much higher yields of the pyrazole 74. The authors described in detail the respective reaction mechanisms... 

In alkaline media, 3-halogeno compounds appear to be less stable 3-chloro-5-phenyl-l,2,4-thiadiazole is decomposed completely by 1 Jf-alcoholic potassium hydroxide and by hydrazine.178 Nucleophilic substitution of the 3-halogen atom by alkoxy groups can be achieved, however, by means of sodium alkoxide in the appropriate alcohol 3-methoxy-, 3-benzyloxy-, and 3-(2 -hydroxyethoxy)-5-phenyl-l,2,4-thiadiazole are obtainable by this route in good yield.178... 

Ethoxy-phenyl)- X/2, 215 (2-Methoxy-benzyl)- X/2, 47 (4-Methoxy-benzyl)- E16a, 432 (Hydrazin-Alkyl.) 2-(l-Methyl-2-oxo-propyliden)-l-(2-butenyliden)- El4b, 660 (Hydrazon + 2-En-al) (2-Phenoxy-ethyl)- E16a, 427 (N-Alkyl.)... 

Amino-3-methoxy-2-(3-pyridyl-methylen-amino)-E15/2, 1809 [(NC)2CH-NH2 + R-CHO] Azetidin 3-Azido-4-(4-methyl-phenyl)-2-oxo- E16b, 371 (Nj-C-CO-Cl + Imin) Furazan 4-(Anilinomethylen-amino)-3-methyl- E8c, 673 (NH2 -> N=CH —NH —Ar) Hydrazin l,2-Bis-[2-pyrrylme-thylen]- -1-oxid X/2, 121 1 H-(Imidazo 1,2-a]-l,3,5-benzotriaze-pin), 10-Hydroxy-2,3-dihydro E9d, 476 [1 -(2-NH2 — Ar) — 2-imino — imidazolidin/COCl2) Imidazo[4,5-f indazol 5,6-Dimethyl-... 

Hydrazin 2-(Diniethylamino-met hy len)-1 -[1 -(2-hydroxy-phenyl)-ethyliden]- El4b, 671 (Hydrazonid-Bildung) Malonsaure (3-Diethylamino-3-methoxy-allyliden)- -dinitril E15/2, 1878 (Amin-Austausch)... 

NICOTINONTTRJLE, l,2-DIHYDRO-4-METHOXY-l -METHYL-2-OXO- see RJKIOO NICOTINOYL HYDRAZINE see NCQ900 1-NICOTINOYLMETHYL-4-PHENYL-PIPERAZINE see NDW520... 

One route to these compounds is the reaction of 3-amino-1,2,4-triazoles (312) with dicyanodiamide (485) to yield (49USP2473797 53JOC1610) 5,1-diamino-l,2,4-triazolo[4,3-a]l,3,5-triazines (486). The 1,3,5-triazine ring of 7-methoxy-3-phenyl-l,2,4-triazolo[4,3-a] 1,3,5-triazine (489) was formed (70T3357) by the direct cyclocondensation of 0-methyl-N-(5-phenyl-l,2,4-triazol-3-yl)urea (488) with methyl diethoxyacetate (487) or triethyl orthoformate. 3,5,7-Triamino-1,2,4-triazolo[4,3-a] 1,3,5-triazine (490) was prepared (53JOC1610 63ZOB1355) in one step by the reaction of two equivalents of dicyanodiamide (485) with one equivalent of hydrazine dihydrochloride. 

The reagent is prepared by heating the diazonium salt (1) in anhydrous benzene. It is an unstable off-white solid. The precursor (I) is prepared from 2-methoxy-2 -nitrodi-phenyl by reduction with hydrazine hydrate in the presence of palladium to give 2-amino-2 -methoxydiphenyl this product is then diazotized with sodium nitrite in... 

Aus l-Acetyl-2-[2-(4-fluor-phenyl)-l-phenyl-ethyliden]-l-isopropyl-hydrazin entsteht beim Er-hitzen mit Kaliumhydroxid in Bis-[2-methoxy-ethyl]-ether auf 80° (Stickstoff-Atmosphare) 4-(4-Fluor-phenyl)-l-isopropyl-5-methyl-3-phenyl-lH-pyrazol (Schmp. 139 140°) in 61%iger Ausbeute958 ... 

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