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Dimethylformamide → 5,7-diethyl-1-(4-nitrobenzyl)-1,6-naphthyridin-2(1H)-one

HRID 487408
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 487408
S(Cl)(Cl)=O.Br[C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1C(O)=O.[N+:15]([C:18]1[CH:24]=[CH:23][C:21](N)=[CH:20][CH:19]=1)([O-:17])=[O:16].[CH3:25][N:26]([CH:28]=[O:29])[CH3:27]>C1(C)C=CC=CC=1.CN1CCCC1=O>[CH2:14]([C:13]1[N:15]=[C:18]([CH2:24][CH3:23])[CH:19]=[C:25]2[C:12]=1[CH:11]=[CH:7][C:28](=[O:29])[N:26]2[CH2:27][C:21]1[CH:23]=[CH:24][C:18]([N+:15]([O-:17])=[O:16])=[CH:19][CH:20]=1)[CH3:6]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 69402-Bromobenzoic acidHCID 74754-NitroanilineHCID 24386Thionyl Chloride

Produkt 1

HCID 189523915,7-diethyl-1-(4-nitrobenzyl)-1,6-naphthyridin-2(1H)-oneAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140
Toluene
Lösungsmittel
2×
HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Thionyl chloride (120.5 g) was added to a stirred mixture of 2-bromobenzoic acid (194 g) in toluene (500 ml) and DMF (5 ml) and the mixture was heated at 80° C. for 4 hours. The solution was cooled to 20° C. and added slowly to a solution of 4-nitroaniline (133.1 g) in toluene (500 ml) and N-methylpyrrolidone (NMP) (120 ml), maintaining the temperature of the reaction mixture between 20°-25° C. The reaction mixture was then stirred for 24 hours when a solid precipitated. Water (360 ml) was added with rigorous stirring and the suspended solid was collected by filtration and washed successively with water, toluene and acetonitrile to give 2-bromo-N-(4-nitrophenyl)benzamide (B) as a solid, in 87% yield; m.p. 200°-202° C.; NMR (d6 -DMSO): 7.4-7.8(m, 7H), 8.0(d, 2H), 8.3(d, 2H), 11.5(brs, 1H); which was used without further purification.

Aufarbeitung

  1. temperatureThe solution was cooled to 20° C.
  2. temperaturemaintaining the temperature of the reaction mixture between 20°-25° C
  3. customprecipitated
  4. additionWater (360 ml) was added
  5. stirringwith rigorous stirring
  6. filtrationthe suspended solid was collected by filtration
  7. washwashed successively with water, toluene and acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-c766c60df76d4f809c51f7ff2829c0b9
Quelldatensatz
uspto-grants-1994_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05294620

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