Phosphorus oxychloride → 4-Chloro-6-(2,6-diethyl-phenyl)-nicotinic acid methyl ester

HRID 1392625Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1392625
[CH3:1][O:2][C:3](=[O:22])[C:4]1[C:9](OC)=[CH:8][C:7]([C:12]2[C:17]([CH2:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:20][CH3:21])=[N:6][CH:5]=1.O=P(Cl)(Cl)[Cl:25]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:22])[C:4]1[C:9]([Cl:25])=[CH:8][C:7]([C:12]2[C:17]([CH2:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:20][CH3:21])=[N:6][CH:5]=1

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 596780886-(2,6-Diethyl-phenyl)-4-methoxy-nicotinic acid methyl ester

Produkt 1

HCID 596781594-Chloro-6-(2,6-diethyl-phenyl)-nicotinic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 6-(2,6-diethyl-phenyl)-4-methoxy-nicotinic acid methyl ester (4.0 g, 13.4 mmol), DMF (10 mL) and POCl3 (10 mL) is heated at 80° C. overnight. The volatile material is removed in vacuo. Ice water, NaHCO3 and hexane (50 mL) are added to the residue. The organic layer is separated and the aqueous layer is extracted with hexane (2×30 mL). The combined organic layer is washed with water, dried, and concentrated. The crude product is purified by silica gel chromatography (1% MeOH in CH2Cl2) to give 4-chloro-6-(2,6-diethyl-phenyl)-nicotinic acid methyl ester. 1H NMR (CDCl3) 9.12 (s, 1H), 7.40 (s, 1H), 7.30 (d, 1H), 7.15 (d, 2H), 4.00 (s, 3H), 2.30 (q, 4H), 1.05 (t, 6H).

Aufarbeitung

  1. customThe volatile material is removed in vacuo
  2. additionIce water, NaHCO3 and hexane (50 mL) are added to the residue
  3. customThe organic layer is separated
  4. extractionthe aqueous layer is extracted with hexane (2×30 mL)
  5. washThe combined organic layer is washed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe crude product is purified by silica gel chromatography (1% MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-e31e624fc99843579bea4955daef520c
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342115B2

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