3-Nitroaniline → 4-chloro-N-(3-nitrophenyl)pyridin-2-amine

HRID 321

Reaktionsgleichung

Reaktionsgleichung von HRID 321
Clc1ccnc(Cl)c1.Nc1cccc([N+](=O)[O-])c1>C1COCCO1.CC(=O)O.CC(=O)O.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C([O-])[O-].[Cs+].[Cs+].[Pd]>O=[N+]([O-])c1cccc(Nc2cc(Cl)ccn2)c1

Komponenten

7

Edukt 2

HCID 74233-NitroanilineHCID 335152,4-Dichloropyridine

Produkt 1

HCID 1022185154-chloro-N-(3-nitrophenyl)pyridin-2-amineAusbeute 47,82 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 10796Cesium carbonateReagenzHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)KatalysatorHCID 4144353Palladium (II) acetateKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

3-Nitroaniline (140 mg, 1.01 mmol), 2,4-dichloropyridine (150 mg, 1.01 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (70.4 mg, 0.12 mmol) and cesium carbonate (660 mg, 2.03 mmol) were stirred in dioxane (5 mL). The mixture was purged with nitrogen for 10 minutes. Palladium(II) acetate (22.76 mg, 0.10 mmol) was added and the mixture heated at 100 °C for 1.5h. The mixture was cooled, filtered and concentrated. The crude product was purified by flash silica chromatography, eluting with 1% MeOH in DCM. Pure fractions were evaporated to dryness to afford 4-chloro-N-(3-nitrophenyl)pyridin-2-amine (121 mg, 47.8 %) as a yellow solid.

Quellen und Nachweise

ORD-Eintrag
ord-703c2a2b287b493ebc27b295a0de91ac
Quelldatensatz
750 AstraZeneca ELN dataset
Originallink
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