Dimethylacetamide → 1-(4-Amino-phenoxy)-5H-benzo[c][1,8]naphthyridin-6-one

HRID 1029118

Reaktionsgleichung

Reaktionsgleichung von HRID 1029118
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[C:6](=[O:12])[NH:7]2.[O-:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Li+].CC([N:28](C)C)=O>O>[NH2:28][C:21]1[CH:22]=[CH:23][C:18]([O:17][C:2]2[CH:11]=[CH:10][N:9]=[C:8]3[C:3]=2[C:4]2[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=2[C:6](=[O:12])[NH:7]3)=[CH:19][CH:20]=1

Komponenten

5

Edukt 3

HCID 31374DimethylacetamideHCID 11815295Lithium phenoxideHCID 581680081-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one

Produkt 1

HCID 581683671-(4-Amino-phenoxy)-5H-benzo[c][1,8]naphthyridin-6-oneAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

1-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (80 mg, 0.35 mmol), and lithium phenoxide (1 mL, 1.04 mmol, 1M solution in THF) were suspended in DMAC (2 mL), and stirred for 4 h at 100° C. The reaction mixture was cooled to room temperature, and diluted with H2O. The resulting precipitate was filtered, washed with H2O, and dried under vacuum to provide 137 (22 mg, 22% yield) as a tan solid. LC-MS (M+H=289, obsd.=289). 1H NMR (400 MHz, d6-DMSO): δ 12.12 (s, 1H), 9.08 (d, 1H), 8.42 (dd, 1H), 8.28 (d, 1H), 7.88 (td, 1H), 7.70 (t, 1H), 7.55 (m, 2H), 7.35 (m, 3H), 6.55 (d, 1H).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with H2O
  4. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ae1c1435f9544b099a3d9e9a1f94cbca
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735584B2

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