Triethylamine → N1-(3-nitro[1,5]naphthyridin-4-yl)-2-methylpropane-1,2-diamine

HRID 81889

Reaktionsgleichung

Reaktionsgleichung von HRID 81889
[NH2:1][CH2:2][C:3]([NH2:6])([CH3:5])[CH3:4].Cl[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][N:16]=2)[N:11]=[CH:10][C:9]=1[N+:18]([O-:20])=[O:19].C(N(CC)CC)C>ClCCl>[N+:18]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:8]=1[NH:1][CH2:2][C:3]([CH3:5])([NH2:6])[CH3:4])=[N:16][CH:15]=[CH:14][CH:13]=2)([O-:20])=[O:19]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 131282-MethylpropylenediamineHCID 131227874-Chloro-3-nitro-1,5-naphthyridine

Produkt 1

HCID 86626700N1-(3-nitro[1,5]naphthyridin-4-yl)-2-methylpropane-1,2-diamineAusbeute 97,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1,2-Diamino-2-methylpropane (8.4 mL, 80.0 mmol) was added to a chilled (0° C.) solution of 4-chloro-3-nitro[1,5]naphthyridine (15.2 g, 72.7 mmol) and triethylamine (20.2 mL, 145 mmol) in dichloromethane (350 mL). The reaction mixture was stirred overnight and then concentrated under reduced pressure. The residue was combined with water (300 mL) and heated at reflux with stirring for 1 hour. The reaction mixture was cooled and filtered. The isolated solid was washed with water and then dried under high vacuum to provide 18.5 g of N1-(3-nitro[1,5]naphthyridin-4-yl)-2-methylpropane-1,2-diamine as a bright yellow powder.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. temperatureheated
  3. temperatureat reflux
  4. stirringwith stirring for 1 hour
  5. temperatureThe reaction mixture was cooled
  6. filtrationfiltered
  7. washThe isolated solid was washed with water
  8. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1364b9624aaf45ae9988adb32894f8cf
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846710B2

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