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Hydrochloric Acid → 2-((4-(2-Fluoro-4-nitrophenoxy)quinolin-7-yl)oxy)-2-methylpropanoic acid

HRID 2277394
Notes
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Reaction equation

HRID 2277394 reaction equation
[F:1][C:2]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:3]=1[O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([OH:15])=[CH:12][CH:13]=2)[N:8]=[CH:7][CH:6]=1.[OH-:23].[Na+].C(Cl)(Cl)Cl.Cl>CC(C)=O.O>[F:1][C:2]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:3]=1[O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][C:14]([CH3:9])([CH3:13])[C:5]([OH:4])=[O:23])=[CH:12][CH:13]=2)[N:8]=[CH:7][CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 14798Sodium HydroxideHCID 1357421754-(2-Fluoro-4-nitrophenoxy)quinolin-7-ol

Product 1

HCID 681940182-((4-(2-Fluoro-4-nitrophenoxy)quinolin-7-yl)oxy)-2-methylpropanoic acidYield 72.5%

Reagents, catalysts & solvents 2

HCID 180
Acetone
Solvent
HCID 962WaterSolvent

Procedure

To a mixture of 4-(2-fluoro-4-nitrophenoxy)quinolin-7-ol (5 g, 16.7 mmol) and NaOH (6.7 g, 166.7 mmol) in acetone (67 mL) was added chloroform (21.9 g, 183.3 mmol) dropwise at room temperature. After the mixture turned brown color, the reaction was heated to reflux for 1 hour. Water (10 mL) was then added to the reaction mixture, and the resulted solution was adjusted to pH 3˜4 with 1 N HCl solution. The resulted mixture was concentrated in vacuo, and then extracted with EtOAc (30 mL). The organic phase was separated, concentrated in vacuo, and treated with 95% EtOH (10 mL). The resulted solid was collected by filtration, dried in vacuo overnight to afford the title compound as a brown solid (2.34 g, 36.4%).

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 1 hour
  3. concentrationThe resulted mixture was concentrated in vacuo
  4. extractionextracted with EtOAc (30 mL)
  5. customThe organic phase was separated
  6. concentrationconcentrated in vacuo
  7. additiontreated with 95% EtOH (10 mL)
  8. filtrationThe resulted solid was collected by filtration
  9. customdried in vacuo overnight

Sources & evidence

ORD record
ord-b790cb05f40d49ed8d64335131d30b20
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09133162B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes