Sodium Bicarbonate → 4'-Acetamido-2-hydroxyacetophenone

HRID 32471

Reaktionsgleichung

Reaktionsgleichung von HRID 32471
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:14])[CH2:12]Br)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C([O-])=[O:16].[K+].C(=O)(O)[O-].[Na+]>CCO>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:14])[CH2:12][OH:16])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 2735122Potassium FormateHCID 12364739N-[4-(2-Bromoacetyl)Phenyl]Acetamide

Produkt 1

HCID 221825304'-Acetamido-2-hydroxyacetophenoneAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
38 °C

Versuchsvorschrift

To a suspension of 4′-acetamido-2-bromoacetophenone 3 (10.0 g, 39 mmol) in EtOH (800 mL), aqueous potassium formate (35.4 g in 200 mL) was added then followed by sodium bicarbonate (3.68 g). The mixture was stirred at 38° C. (inner temp.) for 22 h. The mixture was evaporated in vacuo until the total volume reached to ca. 300 mL The mixture was diluted with ethyl acetate (1200 mL), washed with water (200 mL), then brine (2×400 mL). Aqueous layers were extracted with ethyl acetate (800 mL then 400 mL). Combined organic layer was dried over anhydrous sodium sulfate and then evaporated in vacuo to give crude 4 as a solid (7.17 g, 95%) which was used to the next step without any purification. MS(ES) m/e 194 [M+H].

Aufarbeitung

  1. additionwas added
  2. customThe mixture was evaporated in vacuo until the total volume
  3. additionwas diluted with ethyl acetate (1200 mL)
  4. washwashed with water (200 mL)
  5. extractionAqueous layers were extracted with ethyl acetate (800 mL
  6. dry with materialCombined organic layer was dried over anhydrous sodium sulfate
  7. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e9b276f7adcf4e6382135009aea5fa2d
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427623B2

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