Name: 4-Fluoro-1H-indole-3-carboxylic acid. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 4-Fluoro-1H-indole-3-carboxylic acid, is researched, Molecular C9H6FNO2, CAS is 23077-42-1, about Improved synthesis of some fluoroindoles. Author is Kalir, Asher; Balderman, D..
2,5-F2-C6-H3NO2 (109 g.) was treated with 155 g. NCCH2CO2Et and 31.6 g. Na in 1000 ml. EtOH for 2 hrs. to give 26% 4-fluoroanthro-xanonitrile, m. 70-1°. 2,4-(O2N)FC6H3Me (155 g.) was refluxed 14 hrs. with 196 g. N-bromosuccinimide in 600 ml. CCl4 and 2 g. benzoyl peroxide and treated directly with pyridine to give 198 g. I (X = 4-F), m. 201-2°, and 37 g. 2,4-(O2N)FC6H3-CHBr2, m. 63-4°. I (X = 5-F and 6-F), m. 189-90°, and 202-4°, resp., were similarly obtained in 64 and 71% yield. I (X = 4-F) was treated with 150 g. p-ONC6H4NMe2.HCl in 1 l. EtOH and 720 ml. 2.5N NaOH at <5° for 1 hr., and then treated with 1.5 l. 6N H2SO4 to give 86 g. 2-O2N X C6H3CHO (II) (where X = 4-F), m. 32-3°, via III (X = 4-F), m. 165-6°. The following compounds were similarly prepared (X, % yield II, m.p. II, % yield III, and m.p. III given): 5-F, 86, 94-5°, 92, 155-6°; 6-F, 95, 62-3°, 96, 151-2°. II (X = 6-F) was treated with MeNO2 to give 76% 2,4-F(O2N)C6H3CH:CHNO2, m. 84°, which was catalytically reduced to 34-63% 4-fluoroindole, m. 29-30°, accompanied by IV, m. 200° (decomposition). The method of K. and S. Szara (1963) was used to prepare V (R, % yield, and m.p. given): CHO, 73, 190-1°; CH:CMeNO2, 81, 191-2°; CH2CHMeNH2, 64, 103-5° (HCl salt m. 240-1°, picrate m. 222-3°). 6-Fluoro-3-(2-nitrovinyl)indole, m. 190-2°, and 6-fluorotryptamine m. 83-4°, were similarly prepared in 68 and 51% yield, resp. V (R = CHO) (3.5 g.) was treated with 6 g. KMnO4 in 120 ml. Me2CO at <40° to give 47% V (R = CO2H), m. 273° (decomposition). 5-Fluoro-3-indolecarboxylic acid, m. 234-6° (decomposition), and 6-fluoro-3-indolecarboxylic acid, m. 242-4° (decomposition), were similarly prepared in 54 and 48% yield, resp. V (R = CH2CHMeNH2) was less active than the 5-fluoro derivative, but more active than the 6-fluoro derivative in the activity cage test on mice. If you want to learn more about this compound(4-Fluoro-1H-indole-3-carboxylic acid)Name: 4-Fluoro-1H-indole-3-carboxylic acid, you may wish to communicate with the author of the article,or consult the relevant literature related to this compound(23077-42-1).
Reference:
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