SU513032A1 - The method of obtaining (2- (indolyl-3) 4-carboxyquinol-3-) alkanoic acid - Google Patents

Description

MaKCHNiyMa psi. Yiyuni in oodasg x 268 275 to them and 33U-347 to them. In the HMR-Spokes, the signals of the methylene groups of the alkamoic acid residue are shifted to weaker sexes, which is what they want in their accegular rpyiuinpODOK: karooksilpoy and 4-carboxi-chinolioic. A similar effect of the last group is experienced by a -methyl group of the indole nucleus (in the case of N -metiline), CH1X), which proves the introduction of the quinoline residueK in position 3 of the indole nucleus. Potentiometric titration of the obtained acids reveals two carboxyl groups of various acidity (5-5.8 and 7.9-8.2).

Example 1. 2 (.ormn-3} -4 -carboxychylolinyl-3 J-acetic acid. A mixture of 0.54 g (0, ОО25 mol) 3- (indolyl-3) propionic acid and 0.37 g (О, О025 mole) isatin in 15 ml of a 33% aqueous solution of caustic soda boil for 50 hours, then cooled, diluted with water and filtered. The filtrate is acidified with 25% acetic acid. The yellow precipitated after several hours is filtered off with alcohol. and crystallized from a large volume of alcohol, 2- (indolyl-3) -4-carboxy-quinolinyl-3 acetic acid is obtained, yield 0.49 g (57% of theory), mp 286-287 ° C (from ethanol). UV spectrum (in 1O – NMS | OH) : A nm () 271 (4,21), 340 (3,86). The PMR spectrum in SUNH, Sfm: 4, DA (CHj); doublet 7,78 (2-H-indole); doublet 9.9 O (WH of indole); multiplet 7.40 (about the tones of the benzene ring of the indole); multiplet 8.10 (quinoline protons). I. (here and then in the system: isopropyl alcohol amiac-water, 8: 1 : 1, Silufol) O, 32., 5, 1. Found,%: C 68.9; H 4.0. Chotsmg, 0. Calculated,%: C 69.4; H 4.0. Example 2. 2 - (2-Methylindolyl-3-4-carboxyquinoline-3 acetic acid. In example 1, from 0.58 g (0.0025 mol of 3-2-methylindolyl-3J propionic acid and O, 37 g (O, OO25 mol) of isatin, 2- (2-methylindolylG3) -4-carboxyquinolinyl-3 acetic acid is obtained Yield 0.48 g (53% of theory), mp 321-322 C (decomp. From ethanol).

UV spectrum (in 1O% MaaON) L, d nm

(ob-): 275 (4.10), 331 (3.62).

PMR spectrum with, S ppm; singlet .2.56 (), singlet 10.43 (N Н), singlet 4.33 (CHj), multiplet 7.13 (protons of the indole benzene ring), multiplet 8.10

1x1iu1yyvys protoshl). pKfjj 5.5; pKts.VD; 1 f 0.36.

Found,%: C 69.6; And 4.7.

CsiHibWaOt.

Calculated,%: C 70.0; H 4.4.

Example 3. 2- (1-Methylindolyl-3) -4-carboxyquinoline-3 | acetic acid.

According to Example 1, from 0.58 g (0, O025 mol) 3- {1-methylindolyl-3) -propionic acid and 0.37 g (O, O025 mol) and Pat, and 2- (1-methylindolyl-3 ) -4-carboxypsypolini7 (-3 acetic acid. Yield 0.495 g {55% of theory), so pl. 283-284 C (decomp., From ethanol).

UV spectrum (10% MaOH)

Max.

Ig

(-CqP): 268 (4.33), 347 (4, O8).

ffri), m.p. C (from ethanol).

UV spectrum (in 1O% MaaON) Lnm

S5

Max

): 271 (4.29), 335 (3.86). PMR spectrum of E CFjCOOH, 5 MD: triplets 2.53 3.53 (CH groups), doublets 7.83 (2-H-indoles) and 9.83 (NH), multiplets 7.33 (protons benzene indole rings) MMP spectrum in CPjCOOH, & MD: singlet 3.85 (N-CHj), singlet 4.33 (CH), singlet 7.77 (2-I-indole), multiplet 7.37 (protons of the benzene indole ring), multiplet 8.10 (quinoline). Rf 0.36; pKd15,4; pKd2.7,94. Found,%: C 69.7; H 4.6. , Calculated,%: C 7O, O; H 4.4. Example 4. 2- (1,2-Dimethylindolyl-3) -4-carboxyquinoline-3j acetic acid. This compound was prepared according to Example 1 from 0.59 g (0, O025 mol) of 3- (1,2-dimethylindol-3) propionic acid and 0.37 g (0.0025 mol) of isatin. Output 0.5 g (53% of theory), so pl. 289-29O-C (from ethanol). UV-spectrum (in 10% MaNOH) Lnm (ij): 279 (4.16), 340 (3.72). PMR spectrum in CFjCOOH, 5m.d .: singlet 3.67 (W-CHj), singlet 2.35 (2-CH3), singlet 4.23 (CH), multiplet 7.13 (protons of the benzene indole ring), multiplet 8.1 O (protons of quinoline). Ig O, 37; pKQi5,6; pKjja8,2. Found,%: C 7O, 2; H 4.9. CsaHieNjO. Calculated,%: C 70.6; H 4.8. Example 5. (Indolyl-3) -4-carboxyquinoline-3 propionic acid. In Example 1, (indolyl-3) -4-carboxyquinol-3 propionic acid is obtained from 0.58 g (O, O025 mol) of 4- (indolyl-3) -based acid and 0.37 g (0, O025 mol) of isatin acid. Output 0.4 g (45% of the theo in, OO (quinoline runs). In | 0, .31; .S;, 9. Found,%: C 69.5; I 4.6. Sa I, LO Calculated ,%: C 70.0; II 4.4. Example 6, (1-Megyl1pcholyl-3) -4-carboxy 1ninyl-3 | propnonic acid. This compound was prepared in example 1 of 0.6 g (O, 0025 mol ) 4- (1-megilipdo-lil-3) -mas; shalic acid and 0.37 g (0, O0 mol) isatin. Yield: 0.5 g (53% of theory), mp 301-ЗО2 С (from ethanol). UV spectrum (in 10% WaOH) L max nm (io): 270 (4.14), 345 (3.87). G1L P-spectrum in C1 С0011.2 m.d. triples 2.5O and 3.50 (CH groups), singlet 3.73 (W-CH3), singlet 7.60 (N H indole multiplets 7.17 (protons of the benzene indole ring) and 7.77 (protons of quinols on Br0, 31; pKaj 5.7; 2. Found,%: C 70.2; H 5.2. Calculated,%; C 7O, 6; H 4.8. Example 7. (2-Met and li Idolyl-3) -4-carboxy-quinolinyl-3 PR-lionic acid. In Example 1, from 0.6 g (0.0025 mol of 4- (2-methyl indole and L-3) -buttonic acid and 0.37 g (O, ОО25 mol) isatin get the target acid. The output of 0.37 g (40% of theory), TPL 319-320 C (from ethanol UV spectrum (in 1O% WaOH) L max nm (): 275 ( 4.13), 328 (3.65). B 0.45. Found,%: C 70.3; H 5.1. Calculated,%: C 70.6; H 4.9. Example 8. (2-Atilindi-3) -4-carboxyquinoline-3 oil per acid. This compound is prepared according to Example 1 of O, 65 g (O, OO25 mol) of 5- (2-methylindo-lyl-E) valeric acid and 0.37 g (O, OO25 mol) of isatin. Output O, 4 g (41 T georii), so pl. ..327; (rv, ui., n thanol) .. UV spectrum (at 10: ;; -F g. 1 K / a UH) D m; .. m (): 272 (4.20), 331 (3 , 88). Pj-0.44. Found,%: C 70.8; And 5.4, (. BI ChisleF {o,%: C 71.1; 11 5.1. Formula i; C o fi G g e H c 1. Method of preparing 2- (indoli n-3) -4carboxyquinoli P1; (- 3 alkanoic acids of formula I (CHj)., - COOH where R. and "are the same or different and represent hydrogen or alkyl; H - 2, 3, 4, characterized in that 3 -dolylketoalkanoic acid of the general form 5 -..- CO- (CHg) k-soon where P, and, have the above-mentioned acheni, interact with iz when they are heated in water with silk food and then release the target product. 2. The method according to claim 1, is different that the process is carried out and the boiling point of the reaction onnoy Myo.