Methanol → (7-Fluoro-quinolin-6-yl)-acetic acid methyl ester

HRID 655246Notes

Reaction equation

HRID 655246 reaction equation
F[C:2]1[C:11]([CH2:12][C:13]([OH:15])=[O:14])=[C:10]([F:16])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.OS(O)(=O)=O.[CH3:22]O>C(OCC)(=O)C>[CH3:22][O:15][C:13](=[O:14])[CH2:12][C:11]1[CH:2]=[C:3]2[C:8](=[CH:9][C:10]=1[F:16])[N:7]=[CH:6][CH:5]=[CH:4]2

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 577423352-(5,7-Difluoroquinolin-6-yl)acetic acid

Product 1

HCID 59320292(7-Fluoro-quinolin-6-yl)-acetic acid methyl esterYield 89.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (5,7-difluoro-quinolin-6-yl)-acetic acid (18.6 g, 83.4 mmol) in methanol (200 mL) was added conc. H2SO4 (4.7 mL, 87.0 mmol). The reaction mixture was concentrated to give a brown residue, which was diluted with 200 ml of ethyl acetate, washed with sat. aq. NaHCO3 and brine, then the organic layer was dried over anhydrous Na2SO4, and concentrated to give (7-fluoro-quinolin-6-yl)-acetic acid methyl ester as yellow solid (17.7 g, yield: 89.8%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto give a brown residue, which
  3. washwashed with sat. aq. NaHCO3 and brine
  4. dry with materialthe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5e75f868a01f4c48831bb8fedb09ace0
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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