Hydrochloric Acid → 3-Chloro-4-cyano-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	L-Pyroglutamic Acid	HCID 7405	—
Reactant	4-Bromo-3-chloro-2-(3-fluoro-4-methoxyphenyl)-6-methoxyquinoline	HCID 22020195	—
Product	3-Chloro-4-cyano-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol	HCID 135489108	41%

Reaction Steps

This compound was prepared from 34b according to method F and method G (using Pyr./HCl). Yellow solid; Yield: 41% (for two steps); mp 325-328° C. (dec.); 1H-NMR (300 MHz, DMSO-d6) δ 7.10 (dd, J=8.8, 8.7 Hz, 1H), 7.27 (d, J=2.5 Hz, 1H), 7.43 (dd, J=8.4, 1.4 Hz, 1H), 7.49 (dd, J=9.2, 2.5 Hz, 1H), 7.55 (dd, J=12.2, 2.0 Hz, 1H), 8.04 (d, J=9.1 Hz, 1H), 10.37 (s, 1H), 10.97 (s, 1H); MS (ESI) m/z 313 ([M−H]−), 315 ([M+H]+); Anal. Calcd for C16H8ClFN2O2: C, 61.07; H, 2.56; N, 8.90. Found: C, 60.80; H, 2.57; N, 8.55.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07632845B2
Source dataset	uspto-grants-2009_12
ORD ID	ord-ac099a26acbe4dce91899e5711a6fc7d
Source note	uspto-grants-2009_12