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

HRID 2040439Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2040439
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-e9e3014cce314477ab582d0c4cdd28e1
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08580842B2

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