Hydrochloric Acid → 2-Amino-4-cyano-3-hydroxynitrobenzene

HRID 1441828

Reaktionsgleichung

Reaktionsgleichung von HRID 1441828
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[OH:12])#[N:2].[I-].C[N+:15](C)(C)N.[O-]OOO[O-].[Na+].[Na+].Cl>CS(C)=O>[NH2:15][C:5]1[C:4]([OH:12])=[C:3]([C:1]#[N:2])[CH:8]=[CH:7][C:6]=1[N+:9]([O-:11])=[O:10]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 18683Hydrazinium, 1,1,1-trimethyl-, iodide (1:1)HCID 2861482-Hydroxy-4-nitrobenzonitrileHCID 131725183CID 131725183

Produkt 1

HCID 218754622-Amino-4-cyano-3-hydroxynitrobenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

Compound 477A (0.438 g, 2.67 mmol) was dissolved in 25 mL of DMSO and trimethylhydrazinium iodide (0.534 g, 2.67 mmol) was added. Sodium pentoxide (0.880 g, 8.01 mmol) was added under N2 to give a deep red solution and stirring was continued overnight at rt. The reaction mixture was poured into 50 mL of 10% HCl and extracted with EtOAc (2×25 mL). The combined organic layers were washed with water (25 mL), brine (25 mL), dried over sodium sulfate and concentrated in vacuo to give compound 477B as an oily red solid which was used directly in the next reaction without further purification.

Aufarbeitung

  1. customto give a deep red solution
  2. extractionextracted with EtOAc (2×25 mL)
  3. washThe combined organic layers were washed with water (25 mL), brine (25 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8ce2c56d4c9b4081b634396015df363f
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07655689B2

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