Acetic Acid → N-phenylindan-2-amine

HRID 2167088Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2167088
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=O.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.CCOC(C)=O>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 6115AnilineHCID 119832-IndanoneHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 118068N-phenylindan-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-indanone (5 g, 37.83 mmol) in DCM (135 mL) were successively added aniline (3.4 mL, 37.83 mmol), AcOH (2.16 mL, 37.83 mmol) and Na(OAc)3BH (11.22 g, 52.96 mmol) portion-wise at ice cold conditions. The reaction mixture was stirred at rt for 16 hours. The reaction mixture was then diluted with EtOAc (450 mL) and washed with water (150 mL) and brine (50 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The crude material was purified by Combiflash® chromatography and eluted with 1.7% EtOAc in hexane to obtain compound 7.

Aufarbeitung

  1. washwashed with water (150 mL) and brine (50 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by Combiflash® chromatography
  6. washeluted with 1.7% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-7d782253e5a74e358f80bf82b1f79973
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09044482B2

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