Ammonia methanol → 8-Fluoro-1-oxo-1,2-dihydroisoquinoline-3-carboxamide

HRID 1476813Notes

Reaction equation

HRID 1476813 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]([O:15]C)=O)=[CH:7]2.[NH3:17].CO>>[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]([NH2:17])=[O:15])=[CH:7]2

Participants

3

Reactant 2

HCID 21705897Ammonia methanolHCID 90387081Methyl 8-fluoro-1-oxo-1,2-dihydroisoquinoline-3-carboxylate

Product 1

HCID 903872368-Fluoro-1-oxo-1,2-dihydroisoquinoline-3-carboxamide

Procedure

To a vessel containing NH3/MeOH (140 mL) was added methyl 8-fluoro-1-oxo-1,2-dihydroisoquinoline-3-carboxylate (5 g, 15 mmol). The vessel was sealed and the solution was stirred at RT for 30 minutes and then heated to reflux for 2 hours. The reaction mixture was concentrated in vacuo to give the title compound, which was used without further purification (5 g, 85%). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.26 (s, 1H), 8.32 (s, 1H), 7.92 (s, 1H), 7.82-7.81 (m, 1H), 7.61-7.59 (d, J=8.0 Hz, 1H), 7.41-7.35 (m, 1H).

Workup

  1. customThe vessel was sealed
  2. temperatureheated
  3. temperatureto reflux for 2 hours
  4. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-bf9067d8d1164320a831790b3535ce7f
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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