Methyl 6-chloro-5-nitronicotinate → Methyl 6-((2-ethoxy-2-oxoethyl)(isopropyl)amino)-5-nitronicotinate

HRID 2097871Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2097871
Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[CH:15]([NH:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])([CH3:17])[CH3:16]>ClCCl>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][N:18]([CH:15]([CH3:17])[CH3:16])[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1)[CH3:24]

Komponenten

4

Edukt 2

HCID 346961Methyl 6-chloro-5-nitronicotinateHCID 351625Ethyl 2-((propan-2-yl)amino)acetate

Produkt 1

HCID 58324358Methyl 6-((2-ethoxy-2-oxoethyl)(isopropyl)amino)-5-nitronicotinateAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Methyl 6-chloro-5-nitronicotinate (2 g, 9.23 mmol) was added to ethyl 2-(isopropylamino)acetate (5.0 g, 34.5 mmol) neat while stirring at room temperature. The viscous yellow reaction was heated to 90° C. for one h and then allowed to cool back to room temperature. The reaction was diluted with dichloromethane (20 mL) and purified via column chromatography (220 g SiO2, 20-30% gradient, ethyl acetate in hexanes) to yield the title compound (2.39 g, 83%) as a yellow oil. [M+H] calc'd for C, 14; H, 19; N, 3; O, 6, 326; found, 326.

Aufarbeitung

  1. customThe viscous yellow reaction
  2. temperaturewas heated to 90° C. for one h
  3. temperatureto cool back to room temperature
  4. custompurified via column chromatography (220 g SiO2, 20-30% gradient, ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-beabcc1526a84c6b9a2772b660507db0
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450323B2

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