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

HRID 418489Notes

Reaction equation

HRID 418489 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].C(OCC)(=O)C>[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

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 59515858(R)-2-(6-Chloro-5-nitro-1-oxoisoquinolin-2(1H)-yl)propanamide

Product 1

HCID 59515791(R)-2-(5-Amino-6-chloro-1-oxoisoquinolin-2(1H)-yl)propanamide

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of (R)-2-(6-chloro-5-nitro-1-oxoisoquinolin-2(1H)-yl)propanamide (120 mg, 0.00040 mol) in ethanol (4 mL, 0.07 mol) was added ammonium chloride (200 mg, 0.004 mol) in water (4 mL, 0.2 mol). The reaction was heated at 85° C. and iron (90 mg, 0.002 mol) was added in two portions 5 minutes apart. The reaction was stirred for 30 minutes and ethyl acetate was added and decanted. the solvent was removed under reduced pressureunder reduced pressure to afford the product as a yellow solid.

Workup

  1. customdecanted
  2. customthe solvent was removed

Sources & evidence

ORD record
ord-7e76d2f10efd49289595eccef508528c
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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