Water → N1-(2-chloro-3-nitroquinolin-4-yl)-2-methylpropane-1,2-diamine

HRID 1097553

Reaktionsgleichung

Reaktionsgleichung von HRID 1097553
C(N(CC)CC)C.[Cl:8][C:9]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17](Cl)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1.[NH2:23][CH2:24][C:25]([NH2:28])([CH3:27])[CH3:26].O>CN1CCCC1=O>[Cl:8][C:9]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17]([NH:23][CH2:24][C:25]([CH3:27])([NH2:28])[CH3:26])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 131282-MethylpropylenediamineHCID 27851382,4-Dichloro-3-nitroquinoline

Produkt 1

HCID 86227765N1-(2-chloro-3-nitroquinolin-4-yl)-2-methylpropane-1,2-diamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel2×

Versuchsvorschrift

Triethylamine (75 mL, 0.54 mol) was slowly added to a solution of 2,4-dichloro-3-nitroquinoline (André et al, U.S. Pat. No. 4,988,815, Example 2, 114 g, 0.470 mol) in anhydrous 1-methyl-2-pyrrolidinone (NMP) (450 mL), and the resulting black solution was cooled to 0° C. A solution of 1,2-diamino-2-methylpropane (42 g, 0.54 mol) in anhydrous NMP (42 mL) was added dropwise over a period of three hours. After the addition was complete, the reaction was allowed to warm to ambient temperature, stirred for five hours, and poured slowly into warm water (4 L) with vigorous stirring. A yellow precipitate formed, and the suspension was stirred for one hour at ambient temperature. The precipitate was isolated by filtration and washed with cold water until the filtrate was colorless. The solid was dissolved in dichloromethane (4 L), and the resulting solution was washed sequentially with saturated aqueous sodium carbonate and brine, dried over magnesium sulfate and sodium sulfate, filtered through a layer of CELITE filter agent, and concentrated under reduced pressure to provide 130 g of N1-(2-chloro-3-nitroquinolin-4-yl)-2-methylpropane-1,2-diamine as a bright yellow powder.

Aufarbeitung

  1. additionAfter the addition
  2. additionpoured slowly
  3. customA yellow precipitate formed
  4. stirringthe suspension was stirred for one hour at ambient temperature
  5. customThe precipitate was isolated by filtration
  6. washwashed with cold water until the filtrate
  7. dissolutionThe solid was dissolved in dichloromethane (4 L)
  8. washthe resulting solution was washed sequentially with saturated aqueous sodium carbonate and brine
  9. dry with materialdried over magnesium sulfate and sodium sulfate
  10. filtrationfiltered through a layer of CELITE filter agent
  11. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-489fbcf52ceb43719bcce3ccbb055541
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143270B2

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