Sodium Hydroxide → 3-Amino-2-hydroxybenzonitrile

HRID 612690

Reaktionsgleichung

Reaktionsgleichung von HRID 612690
[C:1]([C:3]1[C:8]([OH:9])=[C:7]([N+:10]([O-])=O)[CH:6]=[CH:5][CH:4]=1)#[N:2].[Sn](Cl)Cl.[OH-].[Na+]>C(O)(=O)C>[NH2:10][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([C:1]#[N:2])[C:8]=1[OH:9]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 124686862-Hydroxy-3-nitrobenzonitrile

Produkt 1

HCID 124686813-Amino-2-hydroxybenzonitrileAusbeute 272,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 6-cyano-2-nitrophenol(600 mg, 1.0 mmol) and tin (II) chloride (3.2 g, 14.4 mmol) in acetic acid(50 mL) was heated at 80° C. under argon. After 2 hours, the starting material has disappeared and the solution was allowed to cool down and then poured into ice. The pH was made slightly basic (pH7-8), by addition of solid NaOH, before being extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4%MeOH/CH2Cl2) gave the desired product(365 mg, 75%). 1H NMR (CD3OD): δ 6.92 (d, 1H), 6.85-6.69 (m, 2H).

Aufarbeitung

  1. temperatureto cool down
  2. additionpoured into ice
  3. extractionbefore being extracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-2f04598f40eb423eb661e123d9d7fc62
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06005008

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