Water → 5-(2-oxo-2,3-dihydro-1H-indol-4-yl)-nicotinic acid

HRID 1826724Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1826724
[Br-].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH:22]1[C:30]2[C:25](=[C:26]([C:31]3[CH:32]=[N:33][CH:34]=[C:35]([CH:39]=3)[C:36]([OH:38])=[O:37])[CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23]1.[OH2:40]>CC(O)(C)C.C(O)C.C(O)(=O)C.[Zn]>[O:40]=[C:23]1[CH2:24][C:25]2[C:30](=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]2[CH:32]=[N:33][CH:34]=[C:35]([CH:39]=2)[C:36]([OH:38])=[O:37])[NH:22]1

Komponenten

8

Edukt 3

HCID 962WaterHCID 21124087PyridiniumtribromideHCID 221354775-(1H-indol-4-yl)-nicotinic acid

Produkt 1

HCID 221353975-(2-oxo-2,3-dihydro-1H-indol-4-yl)-nicotinic acidAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittel2×HCID 702EthanolLösungsmittelHCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

Pyridinium tribromide (90% (Aldrich), 9.8 g, 27.6 mmol) was added portion-wise over 10 minutes to a suspension of 5-(1H-indol-4-yl)-nicotinic acid (2.2 g, 9.2 mmol) in 2-methyl-2-propanol (54 mL), ethanol (36 mL) and acetic acid (108 mL). The mixture was stirred at room temperature for 2 hours and then acetic acid (10 mL) was added. After stirring for an additional hour, water (0.5 mL) and zinc dust (6 g, 92 mmol) were added and stirring was continued for another hour. Residual zinc dust was filtered and washed with methanol. The filtrate was concentrated and the syrupy residue was stirred in water (300 mL) overnight. The solid which formed was filtered, washed with water to remove zinc and pyridine salts and dried under high vacuum to give 2.3 g (98%) of 5-(2-oxo-2,3-dihydro-1H-indol-4-yl)-nicotinic acid.

Aufarbeitung

  1. stirringAfter stirring for an additional hour
  2. stirringstirring
  3. waitwas continued for another hour
  4. filtrationResidual zinc dust was filtered
  5. washwashed with methanol
  6. concentrationThe filtrate was concentrated
  7. stirringthe syrupy residue was stirred in water (300 mL) overnight
  8. customThe solid which formed
  9. filtrationwas filtered
  10. washwashed with water
  11. customto remove zinc and pyridine salts
  12. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-60aac456ae5e4c0ea4cb52e3e5b69b9c
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07053086B2

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