Hydrogen Bromide → 4-Cyano-2-(4-hydroxyphenyl)quinolin-6-ol

Participants

Role	Name	HCID	Charge
Reactant	Hydrogen Bromide	HCID 260	—
Reactant	L-Pyroglutamic Acid	HCID 7405	—
Reactant	4-Cyano-6-methoxy-2-(4-methoxyphenyl)quinoline	HCID 22020213	—
Product	4-Cyano-2-(4-hydroxyphenyl)quinolin-6-ol	HCID 135430315	89%

Reaction Steps

This compound was prepared from 9a using Pyr./HBr according to method I. Yellow solid; Yield: 89%; mp>240° C. (dec.); 1H-NMR (300 MHz, DMSO-d6) δ 6.92 (d, J=8.7 Hz, 2H), 7.30 (d, J=2.6 Hz, 1H), 7.45 (dd, J=9.1, 2.6 Hz, 1H), 8.02 (d, J=9.1 Hz, 1H), 8.13 (d, J=8.7 Hz, 2H), 8.58 (s, 1H), 9.93 (s, 1H), 10.64 (s, 1H): MS (ESI) m/z 261 ([M−H]−), 263 ([M+H]+); Anal. Calcd for C16H10N2O2: C, 73.27; H, 3.84; N, 10.68. Found: C, 71.75; H, 3.86; N, 10.14.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07632845B2
Source dataset	uspto-grants-2009_12
ORD ID	ord-7dd8813a69fa44fdb90c3a8dc6c7a6f3
Source note	uspto-grants-2009_12