Methanol → HCID 20273174, Verbindung

HRID 544143Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 544143
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[C:21]#[N:22])[CH2:13][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]([O-])(=[O:28])[CH3:27].[Na+].[H][H].CO>C(OC(=O)C)(=O)C.[Ni].CCOCC>[C:26]([NH:22][CH2:21][C:20]1[CH:23]=[CH:24][CH:25]=[C:18]([N:14]2[C:15]3[C:11](=[CH:10][C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[CH:17][CH:16]=3)[CH2:12][CH2:13]2)[CH:19]=1)(=[O:28])[CH3:27]

Komponenten

8

Edukt 4

HCID 887MethanolHCID 517045Sodium AcetateHCID 133247163-(5-Benzyloxy-1-indolinyl)benzonitrileHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 20273174HCID 20273174, VerbindungAusbeute 86,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 935NickelKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 7918Acetic AnhydrideLösungsmittel

Versuchsvorschrift

A solution of 1.52 g (4.7 mmole) of 3-(5-benzyloxy-1-indolinyl)benzonitrile of Example 18b in 60 ml acetic anhydride over 0.2 g Raney Nickel (#28 finely divided) and 0.76 g (9.3 mmole, 2 equivalents) sodium acetate was shaken at 50° C. under 50 psi of hydrogen until gas uptake had ceased and TLC analysis showed the reduction to be complete. The catalyst was filtered on a pad of celite and the filtrate was partitioned between chloroform (40 ml) and water (400 ml) and the combined organic portions were washed twice with water (600 ml), aqueous NaHCO3 (two 600 ml portions) and brine, dried over Na2SO4, and concentrated to give an oil. Chromatography on silica gel (80 g) using 1-5% methanol in ether afforded 1.31 g (86.8%) of N-Acetyl-3-(5-benzyloxy-1-indolinyl)benzenemethanamine as an oil.

Aufarbeitung

  1. filtrationThe catalyst was filtered on a pad of celite
  2. customthe filtrate was partitioned between chloroform (40 ml) and water (400 ml)
  3. washthe combined organic portions were washed twice with water (600 ml), aqueous NaHCO3 (two 600 ml portions) and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give an oil

Quellen und Nachweise

ORD-Eintrag
ord-d8ca957bbd0d48ff8209cbe42a75a055
Quelldatensatz
uspto-grants-1984_05
Patentnummer
US04448784

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