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

HRID 1161284Notes

Reaction equation

HRID 1161284 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 reaction went to completion and the solvent was removed under reduced pressure, and the resulting product was dried in vacuum (yellow oil) and was used in the next reaction without any purification. MS m/z=305.4 (M+H).

Workup

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

Sources & evidence

ORD record
ord-867a26d78d85495ea33ebfe824283660
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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