SU509588A1 - Method for preparing imidazo (4,5-c) quinolines - Google Patents

Description

(54) CILOCOFs OF OBTAINING IMIDAZO (4,5-c) CHIPOLINS

one

 This invention relates to a process for the preparation of imidazo (4,5-c) quinoline of the general formula

where R api.Ji;

K - vol., Alkyl, arnl. halogen, nitro; ilkoxy-, caroox.i-, carbalkoxygrunia, which are the initial products in the synthesis of the physiological activity of the active compounds.

News of the quarrodes received (; no quinolines by Scrun, Debier-Miller, Ifitiinger, Friedlandor.

MMH4vr (Mi (; 11gchb receiving - .iigzo (4,5-С) quinolinone, concluded in Rcn: r.TaHOii; ieiuui

4-amino-3-nitroquinolines over a platinum catalyst, followed by condensation: the resulting diaminoquinoline with acetic acid; ianhydride.

The disadvantages of this cn (x: o6a quinolines are the two-stage process, the low yield of the target product and the difficulty of starting; 3,4-D11 amino-quinolines. In addition, it is known that only one representative of imidazo was obtained by the method (4,5-c a) quinoline.

; The aim of the invention is to improve: the progress of the target product and the simplification of the process technology.

 This goal is achieved in that the pyridinium betaines formyl imidazoles are reacted with aromatic amines. I The process is carried out predominantly at 80-118% in an acetic acid relay.

The proposed method allows for the wide variation of 1a: the malleable substituents of both the quinoline and imidazole moieties. I Process olenstadien, progg performed and I allows to learn target products with. High yields (70-80%). The proposed method uses readily available raw materials.

(-Troenia compounds polt rygmy PC-,. UV and NMR spectrum; 1mi. (Xsma reaction.

Dh-

/)

About mzh. -} (L I

Claims (2)

where I and have the above values. Example 1, I-2-oxo-3-phenyl-imidazo-(4,5-c) -quinoline-6-carboxylic acid methyl ester. A mixture of 1.35 g (0.0051 mol) of 1-phenyl-5-formylI- (1-pyridine) -imidazole-2-oxide, 0.65 ml (0.0051 mol) of anthranilic acid methyl ester and 8 ml of acetic acid boil for 15–20 min, then cool and precipitate is separated on a filter. Then from the filtrate with ether planted an additional amount of the product. Crystallized from acetic acid. Get a light yellow crystalline product, t, pl. . The yield of 1.37 g (85%). Found,%: C 67.54; H 4, 13.32. Cl8Hi3 / V303Calculated,%: C 67.71; H 4.07, / V 13,16. Example 2. lH-2-Oxo-3-phenylimidazo (4,5-c) quinoline-6-carboxylic acid. 3.19 g (0.01 mol) of methyl. The 1H-2-oxo-3-phenyl-imidazo ester (4,5-c) quinoline-6-carboxylic acid obtained in Example 1 is heated for 1 hour in a 20% aqueous alkali solution. The reaction mixture is cooled and neutralized with a 10% hydrochloric acid solution. The precipitate is separated, dried and crystallized from acetic acid. Melting point of the desired product. Yield 2.74 g (90%). Found,%: C, 66.7%; H, 3.44 / V 13.63. - spNp zSzZCalculated,%: 066,88 ,; H 3.6Sh L 13.77. Example 3. lH-2-Oxo-3-phenyl-7-ет etylim dao (4,5-c) hinnopin. To 1.325 g (0.005 mol) of 1-phenyl-5-formyl-4-I (1-pyridium) - imidazole-2-oxide dissolved in acetic acid, 0.54 ml (0.005 mol) of m-toluidine and heat are added. (2 hours at 80-90 ° C. cooled reaction) the mass is diluted with water and the precipitated precipitate is crystallized from isopropyl alcohol. A light yellow crystalline pro is obtained,. duct, t. pl. 228-230 Yield 0.96 g {70%). Found, ° C 74,: ij H 4.6; L 15.2 Cl7 l3 3 "Calculated,.: C 74.1 and 4.7 j L 15.3. Example 4. IH-2-Oxo-3-phenylimidazo (4,5-c) quinoline. A mixture of 2.65 g (0.01 mol) of 1-phenyl-5-formyl-4 (1-pyridium) -imidazole-2-oxide and 0.91 ml (0.01 mol) of aniline is boiled for 1 hour in acetic acid. sour ones. The cooled reaction mass is diluted with water. The precipitate is filtered-: and crystallized from isopropyl alcohol, and then from benzene. A yellow crystalline precipitate is obtained, mp. . Yield 1.98 g (). Found,%: C 73.7; H 4.1; fi 16, 2. CigHiiAfgO. Calculated,%: C 73.5; And 4.2; L 16.1. Claim I. Investigation method of imidazo (4,5-с) chimoline of general formula where and is aryl; i-hydrogen, alkyl, aryl, helogen, nitro, alkoxy-, carboxy-, carOal. CoCG, about tl and h and ui and and with. and the fact that, in order to increase the ukhozh uc.Meio500588 five product simplification and process simplification, 2. The method according to claim 1, distinguish and and g teM, trydimievyr b for mimi Formilimi / and added that the process is carried out at RO-118 C in the medium of kg, y (dt in rc aktsik: n aroma with them). iit acids.