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

HRID 655251Notes

Reaction equation

HRID 655251 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH2:12][C:13]([OH:15])=[O:14].OS(O)(=O)=O.[CH3:21]O>C(OCC)(=O)C>[CH3:21][O:14][C:13](=[O:15])[CH2:12][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[F:1])[N:9]=[CH:8][CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 468356122-(7-Fluoroquinolin-6-yl)acetic acid

Product 1

HCID 59320292(7-Fluoro-quinolin-6-yl)-acetic acid methyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (7-fluoro-quinolin-6-yl)-acetic acid (13.4 g, 65.36 mmol) in methanol (140 mL) was added conc.H2SO4 (3.5 mL, 68.63 mmol). The reaction mixture was concentrated to give a brown residue, which was diluted with 100 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 (14.0 g, yield: 98%).

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-a246ffe110d644489761b10db1a7e158
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

Loading…