ChemicalBook CAS DataBase List 4-CHLORO-7-TRIFLUOROMETHYLQUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER

4-CHLORO-7-TRIFLUOROMETHYLQUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER synthesis

6synthesis methods

Product Name:4-CHLORO-7-TRIFLUOROMETHYLQUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER
CAS Number:21168-42-3
Molecular formula:C13H9ClF3NO2
Molecular Weight:303.66

391-02-6 Synthesis

ETHYL 4-HYDROXY-7-(TRIFLUOROMETHYL)QUINOLINE-3-CARBOXYLATE

391-02-6
42 suppliers
$303.80/5g

4-CHLORO-7-TRIFLUOROMETHYLQUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER

21168-42-3
28 suppliers
$234.00/1g

Yield:21168-42-3 93%

Reaction Conditions:

with trichlorophosphate at 70; for 3 h;Large scale;

Steps:

1 Ethyl 4-chloro-7-(trifluoromethyl)quinoline-3-carboxylate [MM-I-05].

The reaction was performed following the same procedure as for MM-I-02 except the reaction was performed in bigger scale. Ethyl 4-hydroxy-7-(trifluoromethyl)quinoline-3- carboxylate MM-I-04 (5 g, 18 mmol) was heated with POCl3 (10 mL) at 70°C for 3 h. MM-I- 05 was obtained as a white solid (5.1 g, 93%): mp 71- 73 °C; 1H NMR (300 MHz, CDCl3) δ 9.30 (s, 1H; H-8), 8.56 (d, J = 8.9 Hz, 1H; H-6), 8.46 (s, 1H; H-3), 7.89 (dd, J = 8.9, 1.5 Hz, 1H; H-1), 4.54 (q, J = 7.1 Hz, 2H; H-20), 1.50 (t, J = 7.1 Hz, 3H; H-19); 13C NMR (75 MHz, CDCl3) δ 163.96 (s), 151.35 (s), 148.54 (s), 143.47 (s), 133.53 (q), 127.84 (s), 127.60 (q), 126.92 (s), 124.69 (s), 124.01 (q), 118.86 (s), 62.45 (s), 14.21 (s); HRMS m/z calculated for C13H9NO2F3Cl 304.0347 found 304.0353.

References:

WO2016/196961,2016,A1 Location in patent:Paragraph 00153-00154

71083-04-0 Synthesis