Ethanol → (S)-2-(5-Amino-6-chloro-1-oxoisoquinolin-2(1H)-yl)propanamide

HRID 418494Notes

Reaction equation

[Cl:1][C:2]1[C:3]([N+:18]([O-])=O)=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([C@@H:13]([CH3:17])[C:14]([NH2:16])=[O:15])[CH:6]=[CH:5]2.C(O)C.[Cl-].[NH4+].O>[Fe]>[NH2:18][C:3]1[C:2]([Cl:1])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][N:7]([C@@H:13]([CH3:17])[C:14]([NH2:16])=[O:15])[C:8]2=[O:12]

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of (S)-2-(6-chloro-5-nitro-1-oxoisoquinolin-2(1H)-yl)propanamide (201 mg, 0.000679 mol), ethanol (10 mL, 0.2 mol), ammonium chloride (363.03 mg, 0.0067868 mol) and water (10 mL, 0.6 mol) was heated at 85° C. Iron (152 mg, 0.00271 mol) was added in three portions, 2 minutes apart and the reaction was stirred at that temperature for 1 hour. The mixture was poured onto dichloromethane (150 mL) and the layers were separated. The organic layer was washed with brine, dried, and the solvent was removed under reduced pressure to afford the product as a light yellow solid.

Workup

additionThe mixture was poured onto dichloromethane (150 mL)
customthe layers were separated
washThe organic layer was washed with brine
customdried
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-eda5eb0be5a342fbbac30256817fe034
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093265B2

Reaction notes

Loading…