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

HRID 1161275Notes

Reaction equation

HRID 1161275 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].ClCCl>[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

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 59515821(R)-2-(6-Chloro-5-nitro-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Product 1

HCID 59515650(R)-2-(5-Amino-6-chloro-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6344DichloromethaneSolvent

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 heated at 85° C. Ammonium chloride (264 mg, 0.00493 mol) in water (7 mL, 0.4 mol) was then added followed by the addition of iron (110 mg, 0.0020 mol) in two portions. The reaction was heated at that temperature for another hour. The reaction mixture was poured into dichloromethane (60 mL) and extracted. The extracts were washed with brine, dried over sodium sulfate and the solvent removed under reduced pressure to obtain the product as a colorless solid. MS m/z=295.5 (M+H).

Workup

  1. temperatureThe reaction was heated at that temperature for another hour
  2. extractionextracted
  3. washThe extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-c5dfcab8920747d9bead7164d90de1f6
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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