Dichloromethane → 2-Methyl-1-((3-nitroquinolin-4-yl)amino)propan-2-ol

HRID 1651530Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1651530
ClCCl.[NH2:4][CH2:5][C:6]([CH3:9])([OH:8])[CH3:7].Cl[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22]>C(N(CC)CC)C>[CH3:7][C:6]([OH:8])([CH3:9])[CH2:5][NH:4][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22]

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 951022-Propanol, 1-amino-2-methyl-HCID 112758084-Chloro-3-nitroquinoline

Produkt 1

HCID 139583422-Methyl-1-((3-nitroquinolin-4-yl)amino)propan-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a stirred solution of 150 ml of dichloromethane, 10 ml of triethylamine and 6.7 g (0.075 mole) of 1-amino-2-methyl-2-propanol was added 10.4 g (0.05 mole) of 4-chloro-3-nitroquinoline. The solution was heated on a steam bath for about one hour then evaporated to remove the solvent. The residue was dissolved in dilute hydrochloric acid and filtered. The filtrate was made basic with concentrated ammonium hydroxide to reprecipitate the product. The product was separated by filtration and recrystallized twice from ethanol to provide the novel yellow solid 2-methyl-1-[(3-nitro-4-quinolinyl)amino]-2-propanol, m.p. 244°-246° C. (dec.). Analysis: Calculated for C13H15N3O3 : %C, 59.8; %H, 5.8; %N, 16.0; Found: %C, 59.8; %H, 5.9; %N 16.1.

Aufarbeitung

  1. temperatureThe solution was heated on a steam bath for about one hour
  2. customthen evaporated
  3. customto remove the solvent
  4. dissolutionThe residue was dissolved in dilute hydrochloric acid
  5. filtrationfiltered
  6. customThe product was separated by filtration
  7. customrecrystallized twice from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-0b21c0aa310f4043b6158688c7207986
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04929624

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