2,4,4-trimethyl-8-nitro-2,4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]oxazin-1-one → 8-amino-2,4,4-trimethyl-2,4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]oxazin-1-one

HRID 633457Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 633457
[CH3:1][N:2]1[C:19](=[O:20])[N:5]2[C:6]3[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[CH:12][C:7]=3[O:8][C:9]([CH3:11])([CH3:10])[C:4]2=[N:3]1>CO.[Pd]>[NH2:16][C:14]1[CH:13]=[CH:12][C:7]2[O:8][C:9]([CH3:11])([CH3:10])[C:4]3[N:5]([C:19](=[O:20])[N:2]([CH3:1])[N:3]=3)[C:6]=2[CH:15]=1

Komponenten

4

Edukt 1

HCID 867045432,4,4-trimethyl-8-nitro-2,4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]oxazin-1-one

Produkt 1

HCID 867045448-amino-2,4,4-trimethyl-2,4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]oxazin-1-oneAusbeute 110,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

2,4,4-Trimethyl-8-nitro-2,4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]oxazin-1-one (249 mg) and 10% Pd—C were suspended in methanol (5 mL). The reaction mixture was stirred at room temperature under H2 atmosphere (1 atm) overnight. The catalyst was filtered off over celite and washed with methanol (5×20 mL). The filtrate was evaporated to give 8-amino-2,4,4-trimethyl-2,4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]oxazin-1-one (245 mg, quant).

Aufarbeitung

  1. filtrationThe catalyst was filtered off over celite
  2. washwashed with methanol (5×20 mL)
  3. customThe filtrate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-d901a16435ab443bbf96d5d141376198
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321763B2

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