Methanol → Methyl 8-fluoro-1-oxo-1,2-dihydroisoquinoline-3-carboxylate

HRID 1476812Notes

Reaction equation

HRID 1476812 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[NH:9][C:8]([C:13]([OH:15])=[O:14])=[CH:7]2.O=S(Cl)Cl.[CH3:20]O>>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[NH:9][C:8]([C:13]([O:15][CH3:20])=[O:14])=[CH:7]2

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 903871878-Fluoro-1-oxo-1,2-dihydroisoquinoline-3-carboxylic acid

Product 1

HCID 90387081Methyl 8-fluoro-1-oxo-1,2-dihydroisoquinoline-3-carboxylateYield 80%

Procedure

To a solution of 8-fluoro-1-oxo-1,2-dihydroisoquinoline-3-carboxylic acid (4 g, 19.3 mmol) in MeOH (100 mL) was added SOCl2 (20 mL) at 0° C. The reaction mixture was stirred at RT for 30 minutes and then heated to reflux for 5 hours. The reaction mixture was subsequently concentrated in vacuo. The crude product was purified by column chromatography eluting with petroleum ether and ethyl acetate (PE/EtOAc=1:1-1:2 gradient) to give a second batch of the title compound (3 g, 80%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.19 (s, 1H), 7.79-7.71 (m, 2H), 7.42-7.38 (m, 2H), 3.89 (s, 3H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 5 hours
  3. concentrationThe reaction mixture was subsequently concentrated in vacuo
  4. customThe crude product was purified by column chromatography
  5. washeluting with petroleum ether and ethyl acetate (PE/EtOAc=1:1-1:2 gradient)

Sources & evidence

ORD record
ord-5b658cbe08a54b6f80875606c0a610d6
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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