Water → 2-Methyl-5-(4-nitrophenoxy)isoindole-1,3-dione

HRID 491071Notes

Reaction equation

HRID 491071 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[NH:13][C:12]3=[O:19])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:24]I.O>CN(C=O)C>[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[N:13]([CH3:24])[C:12]3=[O:19])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 8675015-(4-Nitrophenoxy)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 8835882-Methyl-5-(4-nitrophenoxy)isoindole-1,3-dioneYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A slurry of 5-(4-nitrophenoxy)isoindoline-1,3-dione (A3 Step 2; 1.0 g, 3.52 mmol) and NaH (0.13 g, 5.27 mmol) in DMF (15 mL) was stirred at room temp. for 1 h, then treated with methyl iodide (0.3 mL, 4.57 mmol). The resulting mixture was stirred at room temp. overnight, then was cooled to ° C. and treated with water (10 mL). The resulting solids were collected and dried under reduced pressure to give 5-(4-nitrophenoxy)-2-methylisoindoline-1,3-dione as a bright yellow solid (0.87 g, 83%): TLC (35% EtOAc/65% hexane) Rf0.61.

Workup

  1. temperaturewas cooled
  2. customThe resulting solids were collected
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-4825dc75ffec4d558b5305fbad53894e
Source dataset
uspto-grants-2009_05
Patent number
US07528255B2

Reaction notes

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