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

HRID 1476831Notes

Reaction equation

HRID 1476831 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[C:11](=[O:13])[NH:10][C:9]([C:14]([O:16]C)=O)=[CH:8]2.[NH3:18].CO>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[C:11](=[O:13])[NH:10][C:9]([C:14]([NH2:18])=[O:16])=[CH:8]2

Participants

3

Reactant 2

HCID 21705897Ammonia methanolHCID 90387576Methyl 8-methoxy-1-oxo-1,2-dihydroisoquinoline-3-carboxylate

Product 1

HCID 903870378-Methoxy-1-oxo-1,2-dihydroisoquinoline-3-carboxamide

Conditions

Temperature
50 °C

Procedure

To a vessel containing NH3/MeOH (20 mL) was added methyl 8-methoxy-1-oxo-1,2-dihydroisoquinoline-3-carboxylate (800 mg, 3.43 mmol). The vessel was sealed and the solution was stirred at 50° C. for 16 hours. The reaction mixture was subsequently concentrated in vacuo to give the title compound, which was used without further purification (800 mg). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.22 (s, 1H), 7.80 (s, 1H), 7.66 (t, 1H, J=8.0 Hz), 7.19-7.22 (m, 2H), 7.09 (d, J=8.0 Hz, 1H), 3.85 (s, 3H); ESI-MS m/z [M+H]+219.

Workup

  1. customThe vessel was sealed
  2. concentrationThe reaction mixture was subsequently concentrated in vacuo

Sources & evidence

ORD record
ord-24f9c84525e248e58e78fc4b5287cd74
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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