Phosphorus oxychloride → 4-Chloro-6-(3,4-dimethoxy-phenyl)-[1,5]naphthyridine-3-carboxylic acid ethyl ester

HRID 445786

Reaktionsgleichung

Reaktionsgleichung von HRID 445786
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1O)=[N:13][C:12]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=1)=[CH:11][CH:10]=2)=[O:5])[CH3:2].O=P(Cl)(Cl)[Cl:29]>>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:29])=[N:13][C:12]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=1)=[CH:11][CH:10]=2)=[O:5])[CH3:2]

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 178469508HCID 178469508, Verbindung

Produkt 1

HCID 596197304-Chloro-6-(3,4-dimethoxy-phenyl)-[1,5]naphthyridine-3-carboxylic acid ethyl ester

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

A mixture of 6-(3,4-dimethoxy-phenyl)-4-hydroxy-[1,5]naphthyridine-3-carboxylic acid ethyl ester (Stage 249.1.3, 493 mg, 1.391 mmol) in POCl3 was stirred at 125° C. for 1.5 h. Then the RM was evaporated to dryness. The residue was quenched with saturated aqueous NaHCO3. The suspension was filtered, the cake was washed with water and dried in the vacuum oven to give the title compound as a brown solid. Used for next step without further purification. (HPLC: tR 3.80 min (Method A); M+H=373 MS-ES)

Aufarbeitung

  1. customThen the RM was evaporated to dryness
  2. customThe residue was quenched with saturated aqueous NaHCO3
  3. filtrationThe suspension was filtered
  4. washthe cake was washed with water
  5. customdried in the vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-bf5767b4751b4bd2a0dcaa0785eb9279
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476294B2

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