Methanol → 7-Chloro-3,4-dihydroisoquinolin-1(2H)-one

HRID 1843819Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1843819
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C([O:17][C:18](=O)[NH:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)C.CO>O=P(Cl)(Cl)Cl.C(Cl)Cl>[Cl:28][C:25]1[CH:26]=[C:27]2[C:22]([CH2:21][CH2:20][NH:19][C:18]2=[O:17])=[CH:23][CH:24]=1

Komponenten

6

Edukt 3

HCID 887MethanolHCID 14812Phosphorus oxide (P4O10)HCID 15405334ethyl N-[2-(4-chlorophenyl)ethyl]carbamate

Produkt 1

HCID 186723977-Chloro-3,4-dihydroisoquinolin-1(2H)-oneAusbeute 25.095,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 24813Phosphorus oxychlorideLösungsmittel

Versuchsvorschrift

P2O5 (3.1 g, 0.0495 mmol) was added to a stirred solution of [2-(4-chloro-phenyl)-ethyl]-carbamic acid ethyl ester (2.5 g, 0.01097 mmol) in POCl3 (10 mL) The resulting mixture was heated to reflux for 3 hours. The reaction was monitored by TLC (10% methanol in DCM). The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The concentrate was quenched with chilled water, basified with NaHCO3 solution and extracted with ethylacetate. The organic layer was washed with water, brine solution, dried over Na2SO4 and concentrated under reduced pressure. Purification by column chromatography on silica gel (10% methanol in CHCl3) afforded 500 mg of the product (26.3% yield).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. concentrationconcentrated under reduced pressure
  4. customThe concentrate was quenched with chilled water
  5. extractionextracted with ethylacetate
  6. washThe organic layer was washed with water, brine solution
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customPurification by column chromatography on silica gel (10% methanol in CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-2b00c07b8df449f0af710961f22bf424
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946260B2

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