(5-Fluoro-quinolin-6-yl)-acetic acid tert-butyl ester → (5-Fluoro-quinolin-6-yl)-acetic acid methyl ester

HRID 655271Notes

Reaction equation

HRID 655271 reaction equation
[C:1]([O:5][C:6](=[O:19])[CH2:7][C:8]1[C:9]([F:18])=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)(C)(C)C>[OH-].[Na+]>[CH3:1][O:5][C:6](=[O:19])[CH2:7][C:8]1[C:9]([F:18])=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2

Participants

3

Reactant 1

HCID 68530051(5-Fluoro-quinolin-6-yl)-acetic acid tert-butyl ester

Product 1

HCID 68534543(5-Fluoro-quinolin-6-yl)-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

(5-Fluoro-quinolin-6-yl)-acetic acid tert-butyl ester (5 g, 19 mmol) in 25 ml of aq. NaOH (4N) was heated to reflux for 4 h. The mixture was washed with ethyl acetate and the aqueous layer was acidified to pH 5 with conc. HCl. The resulting precipitate was collected and washed with water and dried in vacuo to return (5-fluoro-quinolin-6-yl)-acetic acid. To this solid was added conc.H2SO4 (1.2 ml) and MeOH (20 ml) and the solution heated to reflux for 6 h. After cooling the solvent was removed in vacuo and the residue purified by flash column chromatography to return the title compound (2.0 g 48%).

Workup

  1. temperatureto reflux for 4 h
  2. washThe mixture was washed with ethyl acetate
  3. customThe resulting precipitate was collected
  4. washwashed with water
  5. customdried in vacuo
  6. additionTo this solid was added conc
  7. temperatureH2SO4 (1.2 ml) and MeOH (20 ml) and the solution heated
  8. temperatureto reflux for 6 h
  9. temperatureAfter cooling the solvent
  10. customwas removed in vacuo
  11. customthe residue purified by flash column chromatography

Sources & evidence

ORD record
ord-71da30cbf15b440ea3b2e9780eeb8075
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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