Ethanol → tert-Butyl 2-(5-amino-6-methyl-1-oxoisoquinolin-2(1H)-yl)ethyl(methyl)carbamate
Reaction equation
[CH3:1][N:2]([CH2:10][CH2:11][N:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH3:25])[C:18]=2[N+:22]([O-])=O)[C:13]1=[O:26])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].C(O)C.[Cl-].[NH4+].O>[Fe]>[NH2:22][C:18]1[C:17]([CH3:25])=[CH:16][CH:15]=[C:14]2[C:19]=1[CH:20]=[CH:21][N:12]([CH2:11][CH2:10][N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:6])([CH3:8])[CH3:7])[C:13]2=[O:26]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
A round bottom flask was charged with tert-butyl methyl(2-(6-methyl-5-nitro-1-oxoisoquinolin-2(1H)-yl)ethyl)carbamate (110 mg, 0.00031 mol) and ethanol (5 mL, 0.08 mol), and the solution was heated at 85° C. Ammonium chloride (300 mg, 0.006 mol) in water (2 mL, 0.09 mol) was added followed by iron (200 mg, 0.003 mol) in two portions. The reaction was stirred for 1 hour and poured onto dichloromethane (200 mL) and extracted. The solvent was removed under reduced pressure and the residue was purified by flash chromatography. to afford the desired product as a yellow oil.
Workup
- additionpoured onto dichloromethane (200 mL)
- extractionextracted
- customThe solvent was removed under reduced pressure
- customthe residue was purified by flash chromatography
Sources & evidence
- ORD record
- ord-d18a5c827e5542658627f235fa0e3ed2
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093265B2
Reaction notes
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