Water → 2-Amino-3-nitro-5-p-tolylpyridine

HRID 722070Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 722070
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].[NH2:17][C:18]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:21](Br)=[CH:20][N:19]=1.O>O1CCOCC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.Cl[Pd]Cl>[NH2:17][C:18]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:21]([C:4]2[CH:5]=[CH:6][C:1]([CH3:10])=[CH:2][CH:3]=2)=[CH:20][N:19]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 79799Tolylboronic acidHCID 1388782-Amino-5-bromo-3-nitropyridine

Produkt 1

HCID 218827162-Amino-3-nitro-5-p-tolylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11050900Dichlorobis(tricyclohexylphosphine)pallium (II)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

0.19 g of dichlorobis(tricyclohexylphosphine)palladium, 0.754 g of 4-tolyl-boronic acid and 12.5 ml of a 2N sodium carbonate solution are added to a solution of 0.93 g of 2-amino-5-bromo-3-nitropyridine in 20 ml of degassed dioxane. The mixture is heated to reflux under N2 for 2.5 hours and, after cooling and addition of water, extracted three times with dichloromethane. The combined organic phases are dried over sodium sulfate and concentrated until a solid begins to precipitate. After addition of petroleum ether, the orange solid is isolated by suction, washed with petroleum ether and dried in vacuo. This gives 0.73 g of the title compound of m.p. 183–184° C. The mass spectrum shows the molecular peak MH+ at 230.1 Da.

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureto reflux under N2 for 2.5 hours
  3. temperatureafter cooling
  4. extractionextracted three times with dichloromethane
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. concentrationconcentrated until a solid
  7. customto precipitate
  8. additionAfter addition of petroleum ether
  9. customthe orange solid is isolated by suction
  10. washwashed with petroleum ether
  11. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1969f66519f14cab80bd060758c0999d
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138399B2

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