Ethanol → HCID 59515926, compound

HRID 418507Notes

Reaction equation

HRID 418507 reaction equation
[C:1]([O:4][CH2:5][CH2:6][NH:7][C:8]1[C:9]([N+:25]([O-])=O)=[C:10]2[C:15](=[CH:16][CH:17]=1)[C:14](=[O:18])[N:13]([CH2:19][CH2:20][O:21][C:22](=[O:24])[CH3:23])[CH:12]=[CH:11]2)(=[O:3])[CH3:2].C(O)C.[Cl-].[NH4+].O>[Fe]>[C:1]([O:4][CH2:5][CH2:6][NH:7][C:8]1[C:9]([NH2:25])=[C:10]2[C:15](=[CH:16][CH:17]=1)[C:14](=[O:18])[N:13]([CH2:19][CH2:20][O:21][C:22](=[O:24])[CH3:23])[CH:12]=[CH:11]2)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 595159322-(2-(2-Acetoxyethyl)-5-nitro-1-oxo-1,2-dihydroisoquinolin-6-ylamino)ethyl acetate

Product 1

HCID 59515926HCID 59515926, compound

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

A mixture of 2-(2-(2-acetoxyethyl)-5-nitro-1-oxo-1,2-dihydroisoquinolin-6-ylamino)ethyl acetate (350 mg, 0.00093 mol), ethanol (20 mL, 0.3 mol), ammonium chloride (496.1 mg, 0.009275 mol) and water (10 mL, 0.6 mol) was added at 85° C. Iron (207 mg, 0.00371 mol) was added in two portions, five minutes apart, and was stirred at that temperature for 1 hour. The reaction mixture was then poured onto methylene chloride (100 mL) and the layers were separated. The organic layer was washed with brine and dried. the solvent was removed under reduced pressureunder reduced pressure and the product was used in the next step without purification.

Workup

  1. additionwas added at 85° C
  2. additionThe reaction mixture was then poured onto methylene chloride (100 mL)
  3. customthe layers were separated
  4. washThe organic layer was washed with brine
  5. customdried
  6. customthe solvent was removed
  7. customthe product was used in the next step without purification

Sources & evidence

ORD record
ord-30174058609845b4892506d10d30d5ff
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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