Hydrochloric Acid → 4-(2-Fluoro-4-nitrophenoxy)quinolin-7-ol

HRID 2277369Notes

Reaction equation

C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:21]=3[F:29])=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.Cl>O1CCOCC1>[F:29][C:21]1[CH:22]=[C:23]([N+:26]([O-:28])=[O:27])[CH:24]=[CH:25][C:20]=1[O:19][C:13]1[C:12]2[C:17](=[CH:18][C:9]([OH:8])=[CH:10][CH:11]=2)[N:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of 7-(benzyloxy)-4-(2-fluoro-4-nitrophenoxy)quinoline (100 g, 256.4 mmol) in dioxane (425 mL) and conc. HCl (425 mL, 5.1 mol) was stirred at 100° C. for 24 hours. The reaction mixture was then cooled to room temperature and solid was collected through filtration. The solid was then suspended in anhydrous EtOH (100 mL) and stirred for 2 hours. The solid was collected and dried in vacuo at 60° C. for 12 hours to give the title compound as a pale solid (73.3 g, 85%).

Workup

temperatureThe reaction mixture was then cooled to room temperature
filtrationsolid was collected through filtration
stirringstirred for 2 hours
customThe solid was collected
customdried in vacuo at 60° C. for 12 hours

Sources & evidence

ORD record: ord-cd4888aa9b26414aa2095c9679650378
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133162B2

Reaction notes

Loading…