Methanol → 2-(3-Fluoroquinolin-8-yl)acetic acid

HRID 2098032Notes

Reaction equation

HRID 2098032 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([F:12])=[CH:7]2.[Cl-].C([O:18][C:19](=[O:22])[CH2:20][Zn+])(C)(C)C.[OH-].[Na+].CO>O1CCOCC1>[F:12][C:8]1[CH:9]=[N:10][C:11]2[C:6]([CH:7]=1)=[CH:5][CH:4]=[CH:3][C:2]=2[CH2:20][C:19]([OH:22])=[O:18]

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 121894698-Bromo-3-fluoroquinolineHCID 178451183HCID 178451183, compound

Product 1

HCID 687559912-(3-Fluoroquinolin-8-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared from 8-bromo-3-fluoroquinoline (568 mg, 2.51 mmol) and 0.5 M (2-Tert-butoxy-2-oxoethyl)zinc(II) chloride according to Protocol P, accept that the ester was converted to the acid using NaOH and MeOH in dioxane. Method [7] retention time 2.39 min by HPLC (M+=206).

Sources & evidence

ORD record
ord-e332cca8319043eea1a8cb745b931289
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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