3-Bromoaniline → HCID 11144112, Verbindung

HRID 1935054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1935054
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:15][CH2:16][CH3:17])=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:18]#[N:19].[Br:20][C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=1)[NH2:24].C(=O)(O)[O-].[Na+]>C(O)C>[Br:20][C:21]1[CH:22]=[C:23]([NH:24][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:15][CH2:16][CH3:17])=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:18]#[N:19])[CH:25]=[CH:26][CH:27]=1

Komponenten

5

Edukt 3

HCID 115623-BromoanilineHCID 516892Sodium BicarbonateHCID 110113054-Chloro-7-ethoxy-6-nitroquinoline-3-carbonitrile

Produkt 1

HCID 11144112HCID 11144112, VerbindungAusbeute 82,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 2.1 g (7.6 mmol) of 4-chloro-7-ethoxy-6-nitro-3-quinolinecarbonitrile and 0.91 ml (8.3 mmol) of 3-bromo aniline in 100 ml ethanol was refluxed under nitrogen for 4.5 hours. The reaction mixture was poured into diluted sodium bicarbonate solution. Ethanol was removed under vacuum. The mixture was diluted with ethyl acetate and the organic layer was separated and dried over sodium sulfate. The solution was concentrated and solid was collected and then washed with hexane. Upon drying, 2.6 g of yellow solid obtained: mass spectrum (electrospray, m/e) M+H 412.8 and 414.9.

Aufarbeitung

  1. temperaturewas refluxed under nitrogen for 4.5 hours
  2. customEthanol was removed under vacuum
  3. additionThe mixture was diluted with ethyl acetate
  4. customthe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationThe solution was concentrated
  7. customsolid was collected
  8. washwashed with hexane
  9. customUpon drying

Quellen und Nachweise

ORD-Eintrag
ord-b6f9af9ddb9c4f15b799e7f8f32e2ad7
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06384051B1

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