Ethanol → (R)-2-(5-Amino-6-chloro-1-oxoisoquinolin-2(1H)-yl)propyl acetate

HRID 418500Notes

Reaction equation

[C:1]([O:4][CH2:5][C@H:6]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Cl:21])[C:14]=2[N+:18]([O-])=O)[C:9]1=[O:22])[CH3:7])(=[O:3])[CH3:2].C(O)C.[Cl-].[NH4+].O>[Fe]>[C:1]([O:4][CH2:5][C@H:6]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Cl:21])[C:14]=2[NH2:18])[C:9]1=[O:22])[CH3:7])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 85 °C

Procedure

A round bottom flask was charged with (R)-2-(6-chloro-5-nitro-1-oxoisoquinolin-2(1H)-yl)propyl acetate (160.0 mg, 0.0004927 mol) and ethanol (7 mL, 0.1 mol), and the reaction was heated at 85° C. Ammonium chloride (264 mg, 0.00493 mol) in water (7 mL, 0.4 mol) was added, followed by iron (110 mg, 0.0020 mol) in two portions. The reaction was stirred at that temperature for one hour. The reaction mixture was then poured onto dichloromethane (60 mL) and extracted. The extracts were washed with brine, dried, and the solvent removed under reduced pressure to afford the product as a colorless solid.

Workup

additionThe reaction mixture was then poured onto dichloromethane (60 mL)
extractionextracted
washThe extracts were washed with brine
customdried
customthe solvent removed under reduced pressure

Sources & evidence

ORD record: ord-845fff6223c84a5eaf0abe5b5e5e0bec
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093265B2

Reaction notes

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