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Carbon Dioxide → 4-[(3-Bromophenyl)amino]-8-dimethylaminomethyl-6-nitro-3-quinolinecarbonitrile

HRID 379116
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 379116
[CH3:1][NH:2][CH3:3].Br[CH2:5][C:6]1[CH:7]=[C:8]([N+:29]([O-:31])=[O:30])[CH:9]=[C:10]2[C:15]=1[N:14]=[CH:13][C:12]([C:16]#[N:17])=[C:11]2[N:18]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Br:28])[CH:23]=1)C(=O)C.C(=O)([O-])[O-].[K+].[K+].C(=O)=O>C1COCC1.CO>[Br:28][C:24]1[CH:23]=[C:22]([NH:18][C:11]2[C:10]3[C:15](=[C:6]([CH2:5][N:2]([CH3:3])[CH3:1])[CH:7]=[C:8]([N+:29]([O-:31])=[O:30])[CH:9]=3)[N:14]=[CH:13][C:12]=2[C:16]#[N:17])[CH:27]=[CH:26][CH:25]=1
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Komponenten

7

Edukt 4

HCID 280Carbon DioxideHCID 674DimethylamineHCID 11430Potassium CarbonateHCID 224666528-Bromomethyl-4-[(3-bromophenyl)-N-acetylamino]-6-nitro-3-quinolinecarbonitrile

Produkt 1

HCID 102026834-[(3-Bromophenyl)amino]-8-dimethylaminomethyl-6-nitro-3-quinolinecarbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a stirred solution of dimethylamine in THF (2.0 M; 115 ml; 230 mmol) at 0° C. was added a solution of 8-bromomethyl 4-[(3-bromophenyl)-N-acetylamino]-6-nitro-quinoline-3-carbonitrile (11.6 g, 23 mmol) in 115 ml of THF during 15 m. After warming to 25° C. the mixture was stirred for 2 h. The THF was evaporated off, and the residue was refluxed in 230 ml of methanol with 12.7 g (92 mmol) of potassium carbonate for 1 h. The mixture was cooled, saturated with CO2, and concentrated. The residue was partitioned with methylene chloride and water. The organic layer was washed with water, dried, and concentrated. The residue was subjected to chromatography on silica gel with methylene chloride-ethyl acetate-methanol-triethylamine to give 6.0 g yellow solid, mp 223-226° C.

Aufarbeitung

  1. customThe THF was evaporated off
  2. concentrationconcentrated
  3. customThe residue was partitioned with methylene chloride and water
  4. washThe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-38ab7493a8af49ebaef4ef9b9094ec89
Quelldatensatz
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06297258B1

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