Water → 3-Chloro-5-fluoro-4-(quinolin-3-yloxy)phenylamine

To a solution of 3-chloro-5-fluoro-4-(quinolin-3-yloxy)nitrobenzene (50.1) (0.980 g) and NH4Cl (1.64 g) in EtOH(50 mL)—H2O (5 mL), was added iron powder (1.92 g). The mixture was heated to reflux for 1 h. After cooling the reaction mixture was filtered through short celite pad. The filtrate was concentrated, diluted with sat.NaHCO3 and extracted with AcOEt (30 mL×3). The combined organic layers were washed with brine and dried over Na2SO4. Concentration of solvent afford crude product, which was purified by column chromatography (silica gel, AcOEt:hexane=1:3) to provide aniline 50.2 (0.420 g) as a colorless solid.

1. temperatureThe mixture was heated
2. temperatureto reflux for 1 h
3. temperatureAfter cooling the reaction mixture
4. filtrationwas filtered through short celite pad
5. concentrationThe filtrate was concentrated
6. additiondiluted
7. extractionNaHCO3 and extracted with AcOEt (30 mL×3)
8. washThe combined organic layers were washed with brine
9. dry with materialdried over Na2SO4
10. customConcentration of solvent afford crude product, which
11. customwas purified by column chromatography (silica gel, AcOEt:hexane=1:3)

ORDレコード

ord-b91882584b0646b89e1b79c8b8bf1b84

出典データセット

uspto-grants-2003_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06583157B2