Phosphorus oxychloride → Methyl 5-chlorobenzo[c][2,6]naphthyridine-8-carboxylate

HRID 604352Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604352
O=[C:2]1[C:11]2[C:6](=[CH:7][N:8]=[CH:9][CH:10]=2)[C:5]2[CH:12]=[CH:13][C:14]([C:16]([O:18][CH3:19])=[O:17])=[CH:15][C:4]=2[NH:3]1.P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:2]1[C:11]2[C:6](=[CH:7][N:8]=[CH:9][CH:10]=2)[C:5]2[CH:12]=[CH:13][C:14]([C:16]([O:18][CH3:19])=[O:17])=[CH:15][C:4]=2[N:3]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 50942139Methyl 5-oxo-5,6-dihydrobenzo[c][2,6]naphthyridine-8-carboxylate

Produkt 1

HCID 25252836Methyl 5-chlorobenzo[c][2,6]naphthyridine-8-carboxylate

Versuchsvorschrift

Methyl 5-oxo-5,6-dihydrobenzo[c][2,6]naphthyridine-8-carboxylate (200 mg, 0.787 mmol) was combined with phosphorus oxychloride (1 mL) and heated to reflux. After 2 hours, LCMS indicated the absence of any starting material. The volatiles were removed under reduced pressure. The residue was taken up in dichloromethane (50 mL) and washed twice with saturated aqueous sodium bicarbonate. The organic phase was dried over sodium sulfate and concentrated on a rotary evaporator to give methyl 5-chlorobenzo[c][2,6]naphthyridine-8-carboxylate (140 mg) as a grayish solid. LCMS (ESI) 273.3 (M+1)+.

Aufarbeitung

  1. temperatureheated to reflux
  2. customThe volatiles were removed under reduced pressure
  3. washwashed twice with saturated aqueous sodium bicarbonate
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated on a rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-92ed3472fba341c8b155e20da6b1abe2
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910600B2

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