Hydrochloric Acid → 7-Hydroxy-3,4-dihydrocarbostyril

HRID 1244029Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1244029
[Cl-].[Al+3].[Cl-].[Cl-].Cl[CH2:6][CH2:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17]C)[CH:12]=1)=[O:9].Cl>>[OH:17][C:13]1[CH:12]=[C:11]2[C:16]([CH2:6][CH2:7][C:8](=[O:9])[NH:10]2)=[CH:15][CH:14]=1

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 27857563-chloro-N-(3-methoxyphenyl)propanamideHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 27857587-Hydroxy-3,4-dihydrocarbostyrilAusbeute 55 %

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

Under nitrogen with outlet to back of hood, added 12.37 g of aluminum chloride powder (0.093 mol) to 7.93 g of 3-Chloro-N-(3-methoxy-phenyl)-propionamide (0.037 mol). Placed in preheated 160° C. sand bath, and heated for 4 hours, raising bath temperature to 200° C., until no more HCl is observed. Cooled to room temperature, chilled in ice bath and cautiously added ice-H2O. Extracted three times with EtOAc, dried (MgSO4), and evaporated under reduced pressure. Purified by flash chromatography on 230–400 Å mesh silica gel, eluting with 1:1 EtOAc/Hexanes to give 3.3 g of beige solid (55%). 1H NMR (400 MHz, CDCl3) δ 2.60 (2H, q, J=6.23 Hz), 2.88 (2H, t, J=6.85 Hz), 6.23 (1H, d, J=2.49 Hz), 6.44 (1H, q, J=2.49 Hz), 7.00 (1H, d, J=8.09 Hz). M/z (APCI+) 163.7 (M+1).

Aufarbeitung

  1. customUnder nitrogen with outlet to back of hood
  2. customPlaced in preheated 160° C.
  3. temperatureheated for 4 hours
  4. temperatureCooled to room temperature
  5. temperaturechilled in ice bath
  6. extractionExtracted three times with EtOAc
  7. dry with materialdried (MgSO4)
  8. customevaporated under reduced pressure
  9. customPurified by flash chromatography on 230–400 Å mesh silica gel
  10. washeluting with 1:1 EtOAc/Hexanes

Quellen und Nachweise

ORD-Eintrag
ord-3ca28b7a947f433caf2432051d3913a9
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07119207B2

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