3-Pentanamine → 4-(1-Ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)nicotinic acid methyl ester

HRID 1245684Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1245684
[CH3:1][O:2][C:3](=[O:22])[C:4]1[C:9](Cl)=[CH:8][C:7]([CH3:11])=[N:6][C:5]=1[O:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=1[CH3:21].[CH2:23]([CH:25]([NH2:28])[CH2:26][CH3:27])[CH3:24]>CS(C)=O>[CH3:1][O:2][C:3](=[O:22])[C:4]1[C:9]([NH:28][CH:25]([CH2:26][CH3:27])[CH2:23][CH3:24])=[CH:8][C:7]([CH3:11])=[N:6][C:5]=1[O:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=1[CH3:21]

Komponenten

4

Edukt 2

HCID 120193-PentanamineHCID 248056514-Chloro-2-(2,4,6-trimethyl-phenoxy)-6-methyl-nicotinic acid methyl ester

Produkt 1

HCID 232165764-(1-Ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)nicotinic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A mixture of 4-chloro-6-methyl-2-(2,4,6-trimethyl-phenoxy)-nicotinic acid methyl ester (500 mg, 1.56 mmol) and 1-ethyl-propyl-amine (0.8 ml) in 1 ml of DMSO was heated at reflux for 15 hours. The mixture was quenched with sat. ammonium chloride and extracted with ethyl acetate. The organic layer was dried and concentrated to give 445.6 mg of yellow solid. The solid was purified through silica gel column chromatography using 1:1 ratio of chloroform:hexane as eluent to give (289 mg, 50%) of the title compound as white crystals, mp 98–102° C.; 1H NMR (CDCl3) δ 8.04 (d, 1H), 6.85 (s, 2H), 6.06 (s, 1H), 3.85 (s, 3H), 3.32 (m, 1H), 2.28 (s, 3H), 2.10 (s, 3H), 2.07 (s, 3H), 1.62 (m, 4H), 0.95 (t, 6H) ppm.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 15 hours
  3. customThe mixture was quenched with sat. ammonium chloride
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was dried
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f05131f41fb34cd9a6ca8c3975fa24af
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07125880B1

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