Sodium Hydroxide → 6-Amino-1,3-dihydro-2H-indol-2-one

HRID 24345

Reaktionsgleichung

Reaktionsgleichung von HRID 24345
O.O.[Sn](Cl)(Cl)(Cl)Cl.[N+:8]([C:11]1[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:12]=1[CH2:20][C:21]([OH:23])=O)([O-])=O.[OH-].[Na+]>C(O)C>[NH2:17][C:15]1[CH:16]=[C:11]2[C:12]([CH2:20][C:21](=[O:23])[NH:8]2)=[CH:13][CH:14]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 2215132,4-Dinitrophenylacetic acidHCID 85782573Tin tetrachloride dihydrate

Produkt 1

HCID 5905386-Amino-1,3-dihydro-2H-indol-2-oneAusbeute 101,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Tin chloride dihydrate (225 g) was added to a solution of 2,4-dinitrophenylacetic acid (22.6 g) in ethanol (450 ml). The mixture was heated at 90° C. for 10 hours. The reaction mixture was cooled and adjusted to pH 11 with 12M sodium hydroxide. The solids were removed by filtration and the filtrate was concentrated. The residue was treated with ethanol (300 ml). Insoluble materials were removed by filtration and washed with ethanol (5×60 ml). The combined ethanol solutions were evaporated and the solid obtained was dried under vacuum to give 15 g of 6-amino-2-oxindole as a brown powder.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. customThe solids were removed by filtration
  3. concentrationthe filtrate was concentrated
  4. additionThe residue was treated with ethanol (300 ml)
  5. customInsoluble materials were removed by filtration
  6. washwashed with ethanol (5×60 ml)
  7. customThe combined ethanol solutions were evaporated
  8. customthe solid obtained
  9. customwas dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-495d6f7339d542228f12d5bb89aa27ff
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855730B2

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