Ethyl 3-acetamido-2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylate → 3-Amino-3,4-dihydroquinolin-2(1H)-one

HRID 413825

Reaktionsgleichung

Reaktionsgleichung von HRID 413825
C([NH:4][C:5]1(C(OCC)=O)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]1=[O:15])(=O)C>Cl>[NH2:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]1=[O:15]

Komponenten

3

Edukt 1

HCID 21853904Ethyl 3-acetamido-2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylate

Produkt 1

HCID 134994273-Amino-3,4-dihydroquinolin-2(1H)-oneAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

3-(N-Acetylamino)-3-carboethoxy-1,2,3,4-tetrahydroquinolin-2-one (0.75 g, 100M %) was suspended in 6N HCl (25 mL) and the mixture was heated to 100° C. for 3 hours. The reaction was cooled, rotoevaporated to a residue and then partitioned between water and ethyl acetate. The water was extracted with ethyl acetate (3×) and the combined ethyl acetate extracts were then washed with water (3×) and then brine (1×). Treatment with MgSO4 followed by rotoevaporation yielded 3-(R,S)-amino-1,2,3,4-tetrahydroquinolin-2-one (72% yield).

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. custompartitioned between water and ethyl acetate
  3. extractionThe water was extracted with ethyl acetate (3×)
  4. washthe combined ethyl acetate extracts were then washed with water (3×)

Quellen und Nachweise

ORD-Eintrag
ord-2857301bb68d43b084979b4317f594dc
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06569851B1

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