Hydrochloric Acid → 4-Quinolinamine, 2-chloro-N-(2-methylpropyl)-3-nitro-

HRID 704848Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 704848
[Cl:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)CC)C.[CH3:23][CH:24]([CH3:27])[CH2:25][NH2:26].Cl>CN(C)C=O>[Cl:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10]([NH:26][CH2:25][CH:24]([CH3:27])[CH3:23])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 6558IsobutylamineHCID 8471TriethylamineHCID 27851382,4-Dichloro-3-nitroquinoline

Produkt 1

HCID 109348134-Quinolinamine, 2-chloro-N-(2-methylpropyl)-3-nitro-Ausbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of 2,4-dichloro-3-nitroquinoline (100 g) and N,N-dimethylformamide (180 mL) was stirred, and triethylamine (42 g, 4 eq) was added dropwise, followed by dropwise addition of 2-methylpropylamine (21.5 g, 0.7 eq). The mixture was stirred at room temperature until the reaction was completed as determined by gas chromatography. Aqueous hydrochloric acid (250 mL, 4N) was added with stirring. The resulting mixture was stirred and cooled to about 0° C. to precipitate the product. The precipitate was filtered, washed with water, and dried at reduced pressure to afford the product 2-chloro-N-(2-methylpropyl)-3-nitro-4-quinolinamine in about 90% yield.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature until the reaction
  2. stirringwith stirring
  3. stirringThe resulting mixture was stirred
  4. customto precipitate the product
  5. filtrationThe precipitate was filtered
  6. washwashed with water
  7. customdried at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-919a4c5a9ee845f980bd4e7e70c3943e
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04988815

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