Ammonia → 4-amino-1-benzyl-3-nitro-1H-pyridin-2-one

HRID 2244798Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2244798
[CH2:1]([N:8]1[CH:13]=[CH:12][C:11](Cl)=[C:10]([N+:15]([O-:17])=[O:16])[C:9]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:19]>C1COCC1>[NH2:19][C:11]1[CH:12]=[CH:13][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9](=[O:18])[C:10]=1[N+:15]([O-:17])=[O:16]

Komponenten

4

Edukt 2

HCID 222AmmoniaHCID 249444631-Benzyl-4-chloro-3-nitropyridin-2(1H)-one

Produkt 1

HCID 219476414-amino-1-benzyl-3-nitro-1H-pyridin-2-oneAusbeute 91,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 1-benzyl-4-chloro-3-nitro-1H-pyridin-2-one (1.30 g, 4.91 mmol) and 28% aqueous ammonia (4.92 g, 39.3 mmol) in THF (30 mL) was stirred at room temp for 17 h. The solvent was evaporated under reduced pressure and water was added to the residue. The resulting precipitate was collected by filtration, and washed with water to give 4-amino-1-benzyl-3-nitro-1H-pyridin-2-one (1.10 g, 91% yield). 1H-NMR (DMSO): δ 8.13 (m, 2H), 7.69 (d, 1H, J=8.0 Hz), 7.31 (m, 5H), 5.94 (d, 1H, J=8.0 Hz), 4.96 (s, 2H). MS: calculated for C12H11N3O3+H 246.1; found: 246.2.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure and water
  2. additionwas added to the residue
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-f2d90cb5b571474bbff89728ef727d9b
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07678909B1

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