ChemicalBook CAS DataBase List 7-CHLORO-1-CYCLOPROPYL-6-FLUORO-4-OXO-1,4-DIHYDRO-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER

7-CHLORO-1-CYCLOPROPYL-6-FLUORO-4-OXO-1,4-DIHYDRO-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER synthesis

14synthesis methods

Product Name:7-CHLORO-1-CYCLOPROPYL-6-FLUORO-4-OXO-1,4-DIHYDRO-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER
CAS Number:86483-54-7
Molecular formula:C15H13ClFNO3
Molecular Weight:309.72

74-96-4 Synthesis

74-96-4
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86393-33-1 Synthesis

7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

86393-33-1
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7-CHLORO-1-CYCLOPROPYL-6-FLUORO-4-OXO-1,4-DIHYDRO-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER

86483-54-7
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Yield:86483-54-7 91%

Reaction Conditions:

Stage #1: 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acidwith potassium carbonate in N,N-dimethyl-formamide; for 0.5 h;
Stage #2: bromure d'ethyle in N,N-dimethyl-formamide; for 10 h;

Steps:

3.1.8. 7-Chloro-1-cyclopropyl-6-uoro-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid EthylEster (8)

General procedure: 7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (7, 17.8mmol)was dissolved in DMF (300 mL) and treated with K2CO3 (28.4 mmol). After 30 min ofstirring, ethyl bromide (135 mmol) was added and stirring continued for 10 h. DMF wasremoved in vacuum and the residue was washed with water (2 50 mL) and filtered. The residue was air-dried and then dried in vacuo [21]. Yield-5 g (91%), white solid, m.p.121-123. 1H-NMR (300 MHz, DMSO-d6) 8.47 (s, 1H), 8.28 (d, J = 4.6 Hz, 1H), 7.98 (d,J = 8.6 Hz, 1H), 4.22 (d, J = 6.5 Hz, 2H), 3.67 (s, 1H), 1.28 (s, 5H), 1.12 (s, 2H). MS m/z 311.6(M + H+).

References:

Lukin, Alexei;Chudinov, Mikhail;Vedekhina, Tatiana;Rogacheva, Elizaveta;Kraeva, Lyudmila;Bakulina, Olga;Krasavin, Mikhail [Molecules,2022,vol. 27,# 15,art. no. 4864]