Hydrochloric Acid → 2-(6,7-Dichloroisatin-1-yl)acetic acid

HRID 1064430

Reaktionsgleichung

Reaktionsgleichung von HRID 1064430
Cl[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][C:6](=[O:12])[C:5]2=[O:13].[H-].[Na+].Br[CH2:17][C:18]([O:20]CC)=[O:19].[ClH:23]>CN(C=O)C>[Cl:11][C:10]1[C:9]([Cl:23])=[C:8]2[C:4]([C:5](=[O:13])[C:6](=[O:12])[N:7]2[CH2:17][C:18]([OH:20])=[O:19])=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 110093415,6-dichloro-1H-indole-2,3-dione

Produkt 1

HCID 222743832-(6,7-Dichloroisatin-1-yl)acetic acidAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 5,6-dichloroisatin (1.0 g, 4.65 mmol) in DMF (20 ml) was cooled in an ice-bath. Sodium hydride (5.11 mmol, 0.20 g 60% dispersion in mineral oil) was added and the mixture was stirred for 20 min. Ethyl 2-bromoacetate (0.37 ml, 5.11 mmol) was added and stirring was continued for 2 hours. The resulting mixture was poured into diluted hydrochloric acid (200 ml, 4M), heated to reflux for 2 hours, filtered, cooled and extracted with ethyl acetate. The organic extract was dried over magnesium sulphate and evaporated to dryness to leave the desired product (0.85 g, 67%).

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for 2 hours
  3. temperatureheated
  4. temperatureto reflux for 2 hours
  5. filtrationfiltered
  6. temperaturecooled
  7. extractionextracted with ethyl acetate
  8. extractionThe organic extract
  9. dry with materialwas dried over magnesium sulphate
  10. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-a256b6b2ea684138a22a5720350a25d6
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06969729B2

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