Water → 1-(4,4-dimethyl-7-nitro-3,4-dihydroquinolin-1(2H)-yl)ethanone

HRID 2219980Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2219980
[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=2)[NH:5][CH2:4][CH2:3]1.[C:16](OC(=O)C)(=[O:18])[CH3:17].O>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=2)[N:5]([C:16](=[O:18])[CH3:17])[CH2:4][CH2:3]1

Komponenten

6

Edukt 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 219614774,4-Dimethyl-7-nitro-1,2,3,4-tetrahydroquinoline

Produkt 1

HCID 590215001-(4,4-dimethyl-7-nitro-3,4-dihydroquinolin-1(2H)-yl)ethanoneAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a stirred solution of 1,2,3,4-tetrahydro-4,4-dimethyl-7-nitroquinoline (Rami et al, WO 03/068749) (500 mg, 2.42 mmol), DMAP (5 mg) in pyridine (2 mL) was added acetic anhydride (0.46 mL, 4.9 mmol). The mixture was stirred at room temperature for 10 h, and then heated at 60° C. for 5 h. After cooling, the mixture was treated with water and extracted with EtOAc. The combined organic layers were washed with sat. aq. NaHCO3, 1N HCl, brine, dried, and evaporated. The residue was purified by chromatography to give a light yellow solid (550 mg, 92%).

Aufarbeitung

  1. temperatureheated at 60° C. for 5 h
  2. temperatureAfter cooling
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with sat. aq. NaHCO3, 1N HCl, brine
  5. customdried
  6. customevaporated
  7. customThe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3918ddff1ace42168345f296e94a4cec
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07414131B2

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