Acetic Acid → N-(6-Bromo-1-oxo-2,3-dihydro-1H-inden-5-yl)acetamide

HRID 1654780Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1654780
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[Br:14])[CH2:10][CH2:9][CH2:8]2)(=[O:3])[CH3:2].C(O)(=[O:17])C>[O-2].[O-2].[O-2].[Cr+6]>[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[Br:14])[C:10](=[O:17])[CH2:9][CH2:8]2)(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 176Acetic Acid2×HCID 104000345-Acetamido-6-bromoindan

Produkt 1

HCID 9993147N-(6-Bromo-1-oxo-2,3-dihydro-1H-inden-5-yl)acetamideAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 10219390chromium (VI) trioxideKatalysator

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 5-acetylamino-6-bromoindane (43.0 g, 0.17 mmol) in glacial acetic acid (400 ml) at 50°-55° C. was added dropwise a solution of chromium trioxide (70.0 g, 0.7 mmol) in 50% aqueous acetic acid (400 mL) over a period of 30 min. After further stirring for 15 min, the mixture was cooled to 0° C. and quenched with 2-propanol (100 mL). Solvent was removed in vacuo. The residue was diluted with water (1 L) and extracted with ethyl acetate (2×500 mL). The combined ethyl acetate layer was washed with 0.5M aqueous NaOH (1 L), brine, dried over anhydrous MgSO4 and concentrated to give 36 g (80%) of the title compound as a light brown solid which was contaminated with about 10% of 5-bromo-6-acetylamino- 1-indanone.

Aufarbeitung

  1. customquenched with 2-propanol (100 mL)
  2. customSolvent was removed in vacuo
  3. additionThe residue was diluted with water (1 L)
  4. extractionextracted with ethyl acetate (2×500 mL)
  5. washThe combined ethyl acetate layer was washed with 0.5M aqueous NaOH (1 L), brine
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-550d828f1d674654b9f9ac754afa4884
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05409944

Notizen zur Reaktion

Wird geladen…