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

HRID 1161269Notes

Reaction equation

HRID 1161269 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].ClCCl>[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 59515834(S)-2-(6-Chloro-5-nitro-1-oxoisoquinolin-2(1H)-yl)propanamide

Product 1

HCID 58973961(S)-2-(5-Amino-6-chloro-1-oxoisoquinolin-2(1H)-yl)propanamide

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6344DichloromethaneSolvent

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. and iron (152 mg, 0.00271 mol) was added in three portions 2 minutes apart. The reaction was stirred at that temperature for 1 hour and poured into dichloromethane (150 mL) and the layers were separated. The organic layer was washed with brine, dried over sodium sulfate and the solvent removed under reduced pressure to obtain the pure product as a light yellow solid. MS m/z=232.5 (M+H).

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-20cf51f2ddd74fb9bf91344bc8ab79d8
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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