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

HRID 1161255Notes

Reaction equation

HRID 1161255 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(OC(=O)C)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

A round bottom flask was charged with (R)-2-(6-chloro-5-nitro-1-oxoisoquinolin-2(1H)-yl)propanamide (120 mg, 0.00040 mol), ethanol (4 mL, 0.07 mol) and ammonium chloride (200 mg, 0.004 mol) in water (4 mL, 0.2 mol) was added and the reaction heated at 85° C. and iron (90 mg, 0.002 mol) was added in two portions 5 minutes apart. The reaction was stirred at that temperature for 30 minutes and ethylacetate was added and decanted. The solvent was removed to get the product as yellow solid. MS m/z=266.2 (M+H).

Workup

  1. additionwas added
  2. customdecanted
  3. customThe solvent was removed

Sources & evidence

ORD record
ord-0730d73c74504705827c3bdbc18bcbe0
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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