Dimethylacetamide → HCID 59549438, Verbindung

HRID 1947774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1947774
[NH2:1][C:2]1[C:10](Br)=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[OH:12])=[CH:4][CH:3]=1.C[C:14]([N:16](C)C)=O>[C-]#N.[Zn+2].[C-]#N.[Zn].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[NH2:1][C:2]1[C:10]([C:14]#[N:16])=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[OH:12])=[CH:4][CH:3]=1

Komponenten

6

Edukt 2

HCID 31374DimethylacetamideHCID 685011896-Amino-7-bromoindan-1-ol

Produkt 1

HCID 59549438HCID 59549438, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 23994ZincKatalysatorHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Katalysator

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A suspension of 6-amino-7-bromoindan-1-ol (1 g, 4.3 mmol), zinc cyanide (290 mg, 2.6 mmol), zinc (140 mg, 2.1 mmol), Pd(dba)3 (10 mol %), and dppf (50 mol %) in dimethylacetamide (8 ml) is heated at 140° C. under nitrogen for six hours. The solvent is distilled off at 100° C. under vacuum, the residue treated with dichloromethane, filtered through Celite, and the filtrate is washed with water. The organic layer is separated, dried over sodium sulfate, filtered, and evaporated. Chromatographic purification by using ethyl acetate/hexane as eluent gives 6-amino-7-cyanoindan-1-ol as solid; LC/MS: 175 (M+1)+.

Aufarbeitung

  1. distillationThe solvent is distilled off at 100° C. under vacuum
  2. additionthe residue treated with dichloromethane
  3. filtrationfiltered through Celite
  4. washthe filtrate is washed with water
  5. customThe organic layer is separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customChromatographic purification

Quellen und Nachweise

ORD-Eintrag
ord-d874f7d45d1648088b03b62111abbfe4
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399490B2

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