Pyrrolidine → 5-phenoxy-1H-indole

HRID 1683279

Reaktionsgleichung

Reaktionsgleichung von HRID 1683279
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][C:5]=1[CH3:17])([O-])=O.[CH2:18](OC(OCC)N(C)C)C.N1CCCC1>CN(C)C=O>[O:10]([C:7]1[CH:6]=[C:5]2[C:4](=[CH:9][CH:8]=1)[NH:1][CH:18]=[CH:17]2)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 31268PyrrolidineHCID 70913Dimethylformamide diethylacetalHCID 27284182-Nitro-5-phenoxytoluene

Produkt 1

HCID 112412535-phenoxy-1H-indoleAusbeute 27,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A solution of 2-nitro-5-phenoxytoluene (2.06 g) in dimethylformamide (30 ml) containing dimethylformamide diethylacetal (1.57 g) and pyrrolidine (0.77 g) was heated at 120° C. for 2 hours. Solvent was removed at reduced pressure and the residue dissolved in methanol. Raney Nickel (one spatula measure) was added followed by hydrazine hydrate (3×0.5 ml portions, one portion every 30 minutes). The mixture was stirred for a further 1 hour after the final portion of hydrazine hydrate was added, the mixture filtered and solvent removed at reduced pressure. The residue was partitioned between water (100 ml) and diethyl ether (100 ml), the organic phase separated and dried (MgSO4), solvent removed at reduced pressure and the residue column chromatographed (silica gel, hexane →10% ethyl acetate/hexane eluant) to give 5-phenoxyindole (0.52 g).

Aufarbeitung

  1. customSolvent was removed at reduced pressure
  2. dissolutionthe residue dissolved in methanol
  3. additionRaney Nickel (one spatula measure) was added
  4. customevery 30 minutes
  5. additionwas added
  6. filtrationthe mixture filtered
  7. customsolvent removed at reduced pressure
  8. customThe residue was partitioned between water (100 ml) and diethyl ether (100 ml)
  9. customthe organic phase separated
  10. dry with materialdried (MgSO4), solvent
  11. customremoved at reduced pressure
  12. customthe residue column chromatographed (silica gel, hexane →10% ethyl acetate/hexane eluant)

Quellen und Nachweise

ORD-Eintrag
ord-6e727b636d3a444ca707d886d637eeac
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05637593

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