Sodium Hydroxide → 3-Amino-2-hydroxybenzophenone

HRID 568047Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 568047
[N+:1]([C:4]1[C:5]([OH:18])=[C:6]([CH:15]=[CH:16][CH:17]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8])([O-])=O.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C>[NH2:1][C:4]1[C:5]([OH:18])=[C:6]([CH:15]=[CH:16][CH:17]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 107053733-Nitro-2-hydroxybenzophenone

Produkt 1

HCID 219605393-Amino-2-hydroxybenzophenoneAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 3-nitro-2-hydroxybenzophenone (600 mg, 2.5 mmol) and tin (II) chloride (1.7 g, 7.5 mmol) in ethanol(50 mL) was heated at 80° C. under argon. After 2 hours, the starting material had 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(490 mg, 92%). 1H NMR (CD3OD): δ 7.65-7.40 (m, 5H), 6.98 (d,1H), 6.86 (d, 1H), 6.67 (t, 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-d0167c16f3954089a9ad3f916aa70f4a
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06180675B2

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