Ammonia → 3-Amino-3-(2-ethoxy-phenyl)-5-methoxy-1,3-dihydro-indol-2-one

HRID 601776Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 601776
Cl[C:2]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH2:21][CH3:22])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][CH3:12])[CH:9]=2)[NH:4][C:3]1=[O:13].[NH3:23]>C(Cl)Cl.C(O)C>[NH2:23][C:2]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH2:21][CH3:22])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][CH3:12])[CH:9]=2)[NH:4][C:3]1=[O:13]

Komponenten

5

Edukt 2

HCID 222AmmoniaHCID 575177773-Chloro-3-(2-ethoxy-phenyl)-5-methoxy-1,3-dihydro-indol-2-one

Produkt 1

HCID 575177783-Amino-3-(2-ethoxy-phenyl)-5-methoxy-1,3-dihydro-indol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3.2 g (10 mmol) of the intermediate from step B were suspended in 40 ml CH2Cl2. 50 ml of a 2M solution of NH3 in ethanol were added and the reaction mixture was stirred for 16 h at ambient temperature. The mixture was poured into an ice/water mixture and the precipitate was separated. The precipitate was redissolved in ethyl acetate. This organic phase was washed with 2M aqueous HCl. The aqueous phase was made alkaline (pH=8-9) and then extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and the solvent was removed in vacuo to yield 1.7 g of the intermediate.

Aufarbeitung

  1. customthe precipitate was separated
  2. dissolutionThe precipitate was redissolved in ethyl acetate
  3. washThis organic phase was washed with 2M aqueous HCl
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-60f02df553c84cccbba38c00638ba906
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902379B2

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