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

HRID 418494
Notes
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Reaction equation

HRID 418494 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

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 1

HCID 23925
Iron
Catalyst

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

  1. additionThe mixture was poured onto dichloromethane (150 mL)
  2. customthe layers were separated
  3. washThe organic layer was washed with brine
  4. customdried
  5. 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

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes