Sodium Hydroxide → 2-Amino-3-chlorophenol

HRID 1385400

Reaktionsgleichung

Reaktionsgleichung von HRID 1385400
[Cl:1][C:2]1[C:3]([N+:9]([O-])=O)=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C>[NH2:9][C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=1[OH:8]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 136221703-Chloro-2-nitrophenol

Produkt 1

HCID 198289622-Amino-3-chlorophenolAusbeute 71,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 3-chloro-2-nitrophenol (250 mg, 1.4 mmol) and tin (II) chloride (1.2 g, 5.3 mmol) in ethanol (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/CH2CH2) gave the desired product (143 mg, 69 %). 1H NMR (CD3OD): d 6.75 (t, 1H), 6.70 (d, 1H), 6.65 (d, 1H).

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-e13dd4cf955d418a81ff421db52f7401
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06262113B1

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