Triethylamine → 2-Chloro-N-(4-methoxybenzyl)-3-nitropyridin-4-amine

HRID 909264Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 909264
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.CCN(CC)CC.[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH2:26])=[CH:23][CH:22]=1>CN(C=O)C>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:26][CH2:25][C:24]2[CH:27]=[CH:28][C:21]([O:20][CH3:19])=[CH:22][CH:23]=2)[CH:5]=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 754524-MethoxybenzylamineHCID 105357732,4-Dichloro-3-nitropyridine

Produkt 1

HCID 534294452-Chloro-N-(4-methoxybenzyl)-3-nitropyridin-4-amineAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2,4-dichloro-3-nitropyridine (12.0 g, 62.2 mmol) in DMF (78 mL) was added NEt3 (10.4 mL, 74.6 mmol) and p-methoxybenzylamine (8.12 ml, 62.18 mmol) at 0° C. After stirring for 10 h at rt, DMF was removed at reduced pressure. The residue was triturated with EtOAc, filtered, washed with EtOAc and hexane, and dried to afford 2-chloro-N-(4-methoxybenzyl)-3-nitropyridin-4-amine (9.29 g, 51%). Additional product (8.0 g, 44%) was obtained by column chromatography (SiO2, eluent) from the filtrates.

Aufarbeitung

  1. customDMF was removed at reduced pressure
  2. customThe residue was triturated with EtOAc
  3. filtrationfiltered
  4. washwashed with EtOAc and hexane
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c67a54d9294a4ba18731161673050a33
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017780B1

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