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

HRID 2277369
Notes
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Reaction equation

HRID 2277369 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 681938637-(Benzyloxy)-4-(2-fluoro-4-nitrophenoxy)quinoline

Product 1

HCID 1357421754-(2-Fluoro-4-nitrophenoxy)quinolin-7-olYield 95.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

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

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. filtrationsolid was collected through filtration
  3. stirringstirred for 2 hours
  4. customThe solid was collected
  5. 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

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes