Phosphorus oxychloride → Methyl 2-chloroquinoline-4-carboxylate

HRID 1761000

Reaktionsgleichung

Reaktionsgleichung von HRID 1761000
[C:1]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7](=O)[CH:6]=1)([O:3][CH3:4])=[O:2].O=P(Cl)(Cl)[Cl:18]>C1(C)C=CC=CC=1>[Cl:18][C:7]1[CH:6]=[C:5]([C:1]([O:3][CH3:4])=[O:2])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 1816364-Quinolinecarboxylic acid, 1,2-dihydro-2-oxo-, methyl ester

Produkt 1

HCID 5202936Methyl 2-chloroquinoline-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A stirred solution of 4-carbomethoxy quinolin-2-one (prepared as shown in Method D (1.76 g, 9 mmol), POCl3 (4.6 g, 30 mmol) in toluene (40 mL) was heated at reflux for 2 h then allowed to cool to room temperature and poured into ice water (50 mL). The mixture was extracted with ethyl acetate (3×50 mL). The organics were combined, washed with water, brine, dried (MgSO4) and concentrated in vacuo to afford the desired 2-chloro-4-carbomethoxyquinoline lv (1.50 mg). 1H NMR (DMSO-d6) δ 8.54 (d, J=8 Hz, 1H), 8.03-8.06 (m, 1H), 7.89-7.94 (m, 2H), 7.75-7.77 (m, 1H), 3.98 (s, 3H); ESI-MS m/z 222.1 (100, M+H+).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. extractionThe mixture was extracted with ethyl acetate (3×50 mL)
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9c8c8e1d8c7345c6a0118c758b1e273e
Quelldatensatz
uspto-grants-2005_01
Patentnummer
US06846834B2

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