Ethanol → 2-Methylamino3-nitro-6-phenylpyridine

HRID 55541

Reaktionsgleichung

Reaktionsgleichung von HRID 55541
C(=O)([O-])[O-].[Na+].[Na+].Cl[C:8]1[N:13]=[C:12]([NH:14][CH3:15])[C:11]([N+:16]([O-:18])=[O:17])=[CH:10][CH:9]=1.B([O-])([O-])O[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O)C>[OH-].[OH-].[Pd+2].C1(C)C=CC=CC=1>[CH3:15][NH:14][C:12]1[C:11]([N+:16]([O-:18])=[O:17])=[CH:10][CH:9]=[C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:13]=1

Komponenten

7

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 107500946-chloro-N-methyl-3-nitropyridin-2-amineHCID 19793864Phenylborate

Produkt 1

HCID 104895752-Methylamino3-nitro-6-phenylpyridineAusbeute 7.773,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

50 ml of a 2N aqueous solution of sodium carbonate and 0.34 g of 20% w/w palladium hydroxide on charcoal were added to a solution of 5.0 g of 6-chloro-2-methylamino-3-nitropyridine (prepared as described in Preparation 66) and 3.9 g of phenyl borate in 80 ml of a 1:1 by volume mixture of ethanol and toluene, and the resulting mixture was stirred at 105° C. for 4.5 hours. At the end of this time, the reaction mixture was filtered to remove the palladium hydroxide on charcoal. The filtrate was concentrated by evaporation under reduced pressure, and the concentrate was diluted with water, after which it was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate, after which the solvent was removed by distillation under reduced pressure. The residue was crystallized by trituration with ethanol, to give 475 g of the title compound, melting at 98°-99° C.

Aufarbeitung

  1. filtrationAt the end of this time, the reaction mixture was filtered
  2. customto remove the palladium hydroxide on charcoal
  3. concentrationThe filtrate was concentrated by evaporation under reduced pressure
  4. additionthe concentrate was diluted with water
  5. extractionafter which it was extracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customafter which the solvent was removed by distillation under reduced pressure
  9. customThe residue was crystallized by trituration with ethanol

Quellen und Nachweise

ORD-Eintrag
ord-3d62ed38c2974e79a7fb0852201ac7ad
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624935

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