Dichloromethane → (R)-2-(6-Methyl-5-nitro-1-oxoisoquinolin-2(1H)-yl)propyl acetate

HRID 418486Notes

Reaction equation

HRID 418486 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]=[C:10]([CH3:18])[C:11]=2[N+:15]([O-:17])=[O:16])[C:6]1=[O:19])[CH3:4].C(Cl)Cl.[C:23](OC(=O)C)(=[O:25])[CH3:24].C(N(CC)CC)C>CN(C)C1C=CN=CC=1>[C:23]([O:1][CH2:2][C@H:3]([N:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH3:18])[C:11]=2[N+:15]([O-:17])=[O:16])[C:6]1=[O:19])[CH3:4])(=[O:25])[CH3:24]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 59515931(R)-2-(1-hydroxypropan-2-yl)-6-methyl-5-nitroisoquinolin-1(2H)-one

Product 1

HCID 59515707(R)-2-(6-Methyl-5-nitro-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a solution of (R)-2-(1-hydroxypropan-2-yl)-6-methyl-5-nitroisoquinolin-1 (2H)-one (4.8 g, 0.018 mol) in methylene chloride (100 mL, 2 mol) was added acetic anhydride (7 g, 0.07 mol), triethylamine (10 g, 0.1 mol) and 4-Dimethylaminopyridine (20 mg, 0.0002 mol). The mixture was stirred at room temperature for 1 hour, washed with 1N hydrochloric acid and brine, and dried. The volatiles were removed under reduced pressure and the residue was purified by column chromatography to afford a yellow-brown oil.

Workup

  1. washwashed with 1N hydrochloric acid and brine
  2. customdried
  3. customThe volatiles were removed under reduced pressure
  4. customthe residue was purified by column chromatography
  5. customto afford a yellow-brown oil

Sources & evidence

ORD record
ord-ed3289c5d8a9448f83378dae310a04d0
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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