Hydrochloric Acid → 1-Hydroxy-6-nitro-2-indolinone

HRID 1007371

Reaktionsgleichung

Reaktionsgleichung von HRID 1007371
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[CH2:13][C:14]([OH:16])=O)([O-])=[O:2].Cl.O.O.[Sn](Cl)Cl>C(O)C.O>[OH:2][N:1]1[C:4]2[C:5](=[CH:6][CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=2)[CH2:13][C:14]1=[O:16]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrate2×HCID 2215132,4-Dinitrophenylacetic acid

Produkt 1

HCID 225695621-Hydroxy-6-nitro-2-indolinone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

2.0 g of 2,4-dinitrophenylacetic acid (prepared according to J: Chem. Soc. 1948, 1717) are dissolved in 40 ml ethanol and 6.0 ml of conc. hydrochloric acid and 4.1 g of tin-(II)-chloride-dihydrate are added in batches at ambient temperature. The mixture is stirred for 12 hours at ambient temperature and for 4 hours at 60° C. After cooling another 2.0 g of tin-(II)-chloride-dihydrate are added and the mixture is stirred for another 12 hours at ambient temperature. The reaction mixture is diluted with water, extracted with methylene chloride and the organic phase is dried over sodium sulphate. After elimination of the solvent the residue is triturated with ether and the precipitate is filtered off.

Aufarbeitung

  1. additionare added
  2. stirringthe mixture is stirred for another 12 hours at ambient temperature
  3. extractionextracted with methylene chloride
  4. dry with materialthe organic phase is dried over sodium sulphate
  5. customAfter elimination of the solvent the residue is triturated with ether
  6. filtrationthe precipitate is filtered off

Quellen und Nachweise

ORD-Eintrag
ord-8941d20d92524b6298ec0a406b10806a
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06794395B1

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