Water → 5-Chloro-2-methyl-6-nitroisoindoline-1,3-dione

HRID 69374

Reaktionsgleichung

Reaktionsgleichung von HRID 69374
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:9](=[O:16])[NH:8][C:7]2=[O:17].[CH3:18]I.O>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:9](=[O:16])[N:8]([CH3:18])[C:7]2=[O:17]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 28011294-Chloro-5-nitrophthalimide

Produkt 1

HCID 542627675-Chloro-2-methyl-6-nitroisoindoline-1,3-dioneAusbeute 73,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

NaH (5.30 g, 0.132 mol) was added in portions to a solution of 5-chloro-6-nitroisoindoline-1,3-dione (20.0 g, 88.27 mmol) in 100 mL of anhydrous DMF at 0° C. under argon. The reaction mixture was then stirred at rt for 3 h. MeI (15.0 g, 106 mol) was added dropwise via a syringe at rt under argon. The resulted mixture was stirred for 6 h at rt, hydrolyzed by adding 200 mL of water. The brown precipitate was isolated, washed with water and dried under vacuum. The solid was purified by column chromatography (silica-gel, CH2Cl2/Acetone=19/1 v/v) to give a yellow solid product, 15.6 g, 73.6% yield. MS: 239.2 [M−H]−. 1H NMR (DMSO-d6, 500 MHz): δ 8.54 (s, 1H), 8.32 (s, 1H), 3.07 (s, 3H).

Aufarbeitung

  1. stirringThe resulted mixture was stirred for 6 h at rt
  2. customThe brown precipitate was isolated
  3. washwashed with water
  4. customdried under vacuum
  5. customThe solid was purified by column chromatography (silica-gel, CH2Cl2/Acetone=19/1 v/v)
  6. customto give a yellow solid product, 15.6 g, 73.6% yield

Quellen und Nachweise

ORD-Eintrag
ord-9c68a90dd0a749e0bd484d9fe7b8b62f
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822500B2

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