Dichloromethane → (R)-2-(5-Nitro-1-oxoisoquinolin-2(1H)-yl)propyl acetate

HRID 418482Notes

Reaction equation

HRID 418482 reaction equation
[OH:1][CH2:2][C@H:3]([N:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N+:15]([O-:17])=[O:16])[C:6]1=[O:18])[CH3:4].[C:19](OC(=O)C)(=[O:21])[CH3:20].C(N(CC)CC)C.C(Cl)Cl>CNC1(NC)C=CN=CC1>[C:19]([O:1][CH2:2][C@H:3]([N:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N+:15]([O-:17])=[O:16])[C:6]1=[O:18])[CH3:4])(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 59515694(R)-2-(1-hydroxypropan-2-yl)-5-nitroisoquinolin-1(2H)-one

Product 1

HCID 59515745(R)-2-(5-Nitro-1-oxoisoquinolin-2(1H)-yl)propyl acetateYield 100%

Reagents, catalysts & solvents 1

HCID 865890494,4-DimethylaminopyridineCatalyst

Procedure

(R)-2-(1-hydroxypropan-2-yl)-5-nitroisoquinolin-1(2H)-one (19 g, 0.073 mol), acetic anhydride (10 g, 0.1 mol), triethylamine (30 g, 0.3 mol), 4,4-dimethylaminopyridine (200 mg, 0.002 mol) and methylene chloride (500 mL, 8 mol) were stirred at room temperature overnight. The solvents were removed under reduced pressure and the residue was purified flash chromatography to afford the title compound as a yellow oil (21 g, 100% yield).

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe residue was purified flash chromatography

Sources & evidence

ORD record
ord-1e57c0c102cc4864b9859bd7cf2b4d3b
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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