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

HRID 418516Notes

Reaction equation

HRID 418516 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].N1C=CC=CC=1.[C:26](OC(=O)C)(=[O:28])[CH3:27].C(Cl)Cl>>[C:26]([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:28])[CH3:27]

Participants

5

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 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

Procedure

A mixture of (R)-2-(1-hydroxypropan-2-yl)-6-methyl-5-nitroisoquinolin-1-(2H)-one (100.0 mg, 0.0003813 mol), pyridine (0.062 mL, 0.00076 mol), acetic anhydride (0.0432 mL, 0.000458 mol) and methylene chloride (5 mL, 0.08 mol) was stirred at room temperature overnight. The solvent was removed under reduced pressure, and the resulting product was dried under vacuum (yellow oil) and was used in the next step without any purification.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe resulting product was dried under vacuum (yellow oil)
  3. customwas used in the next step without any purification

Sources & evidence

ORD record
ord-b26c6e8d35f1446193091593a9011d9e
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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