Hydrochloric Acid → HCID 68753493, compound

HRID 1519862Notes

Reaction equation

HRID 1519862 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[C:4]([CH2:12][C:13]([O:15]C(C)(C)C)=[O:14])[CH:3]=1.FC1C=C(CC(OC(C)(C)C)=O)C=C2C=1C=CC=N2.Cl>C(O)(=O)C.O1CCOCC1>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[C:4]([CH2:12][C:13]([OH:15])=[O:14])[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 68756531HCID 68756531, compoundHCID 687576001,1-Dimethylethyl 7-fluoro-5-quinolineacetate

Product 1

HCID 68753493HCID 68753493, compoundYield 6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 2-(7-fluoroquinolin-5-yl)acetate and tert-butyl 2-(5-fluoroquinolin-7-yl)acetate (0.50 g, 1.91 mmol) in acetic acid (5 mL) was added 4M hydrochloric acid in 1,4-dioxane (10 mL). The reaction mixture was heated in an oil bath set at 60° C. under condenser with N2 (g) inlet overnight. The mixture was concentrated under reduced pressure and purified by flash chromatography (silica, 60:40 ethyl acetate/hexane followed by 20:80 methanol/dichloromethane). Further purification and separation by prep HPLC yielded the single regio-isomer 2-(7-fluoroquinolin-5-yl)acetic acid (0.025 g, 6%). Retention time (min)=0.337, method [4], MS(ESI) 206.1 (M+H).

Workup

  1. temperatureThe reaction mixture was heated in an oil bath
  2. concentrationThe mixture was concentrated under reduced pressure
  3. custompurified by flash chromatography (silica, 60:40 ethyl acetate/hexane followed by 20:80 methanol/dichloromethane)
  4. customFurther purification and separation by prep HPLC

Sources & evidence

ORD record
ord-7c55d97b477644bf9885f74f1eb41dfb
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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