Dichloromethane → HCID 22397142, Verbindung

HRID 1070643Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1070643
[Cl:1][C:2]1[N:3]=[C:4]([CH3:19])[CH:5]=[C:6]2[C:11]=1[N:10]([CH3:12])[CH:9]=[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:7]2=[O:18].BrN1C(=O)CCC1=O.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.C(Cl)Cl>ClC(Cl)C.CN(C=O)C>[Cl:1][C:2]1[N:3]=[C:4]([CH2:19][N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[CH:5]=[C:6]2[C:11]=1[N:10]([CH3:12])[CH:9]=[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:7]2=[O:18]

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 8083MorpholineHCID 67184N-bromobutanimideHCID 22397150HCID 22397150, Verbindung

Produkt 1

HCID 22397142HCID 22397142, VerbindungAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

Ethyl 8-chloro-1,6-dimethyl-4-oxo-1,4-dihydro[1,7]naphthyridine-3-carboxylate (Preparation 44, 0.62 g) and N-bromosuccinimide (0.45 g) are dissolved in dichloro-ethane (100 mL). The solution is subjected to light by shining a 650W sunlamp with stirring for 25 minutes. Solvent is evaporated and the crude solid obtained is dissolved in DMF (15 mL). Morpholine (0.86 g) is added and the mixture stirred for 18 hours. The mixture is poured into CH2Cl2 (200 mL) and then washed with water (3×200 mL). The organics are dried with Na2SO4, filtered and the solvent evaporated. The crude solid is chromatographed with MeOH/CH2Cl2 (0-5%) to obtain 0.32 g (40%) of the title compound as a light orange solid. Physical characteristics: MS (ESI+) m/z 366 (M+H).

Aufarbeitung

  1. customSolvent is evaporated
  2. customthe crude solid obtained
  3. stirringthe mixture stirred for 18 hours
  4. washwashed with water (3×200 mL)
  5. dry with materialThe organics are dried with Na2SO4
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customThe crude solid is chromatographed with MeOH/CH2Cl2 (0-5%)

Quellen und Nachweise

ORD-Eintrag
ord-8e3ba4a9b4f047418bb102589132eb3f
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06903097B2

Notizen zur Reaktion

Wird geladen…