Ammonia methanol → 7-Chloro-1-oxo-1,2-dihydroisoquinoline-3-carboxamide

HRID 1476818Notes

Reaction equation

HRID 1476818 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:13]([O:15]CC)=O)[NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[NH3:18].CO>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:13]([NH2:18])=[O:15])[NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 21705897Ammonia methanolHCID 90386855Ethyl 7-chloro-1-oxo-1,2-dihydroisoquinoline-3-carboxylate

Product 1

HCID 903871057-Chloro-1-oxo-1,2-dihydroisoquinoline-3-carboxamideYield 38%

Procedure

Ethyl 7-chloro-1-oxo-1,2-dihydroisoquinoline-3-carboxylate (580 mg, 2.30 mmol) was dissolved in NH3/MeOH(4.0M, 15 mL) and the reaction mixture was stirred at RT overnight. The solvent was removed in vacuo. The resulting residue was washed with petroleum ether and dried to give the title compound (200 mg, 38%). ESI-MS m/z [M+H]+223.1.

Workup

  1. customThe solvent was removed in vacuo
  2. washThe resulting residue was washed with petroleum ether
  3. customdried

Sources & evidence

ORD record
ord-e9268d116d794627aca07daa61a2164a
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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