Ammonium Chloride → 6-Amino-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one

HRID 519206Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 519206
[CH3:1][CH:2]1[N:15]2[C:6]([CH2:7][O:8][C:9]3[C:14]2=[CH:13][C:12]([N+:16]([O-])=O)=[CH:11][CH:10]=3)=[N:5][NH:4][C:3]1=[O:19].[Cl-].[NH4+]>CO.[Zn]>[NH2:16][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][C:6]1[N:15]2[CH:2]([CH3:1])[C:3](=[O:19])[NH:4][N:5]=1

Komponenten

5

Edukt 2

HCID 25517Ammonium ChlorideHCID 86727620HCID 86727620, Verbindung

Produkt 1

HCID 867272916-Amino-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-oneAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 4-methyl-6-nitro-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (10 g, 38.2 mmol) and ammonium chloride (20.5 g, 382.0 mmol) in MeOH (200 mL) was added zinc powder (24.8 g, 382.0 mol) and the resulting mixture was stirred for 24 h at 25° C. The reaction mixture was filtered and the filtrate was washed with methanol (5×30 mL). The filtrate was combined and concentrated in vacuo and the residue was purified by chromatography on silica gel (eluting with 10% MeOH in DCM) to give 6-amino-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (6.8 g, 77%) as a yellow solid. 1H NMR (DMSO-d6, 400 MHz): δ 10.72 (s, 1H), 6.67 (d, J=8.4 Hz, 1H), 6.42 (d, J=2.4 Hz, 1H), 6.15 (q, J=8.4 Hz, J=2.4 Hz, 1H), 4.82 (brs, 2H), 4.52 (q, J=6.4 Hz, 1H), 4.43 (d, J=12.8 Hz, 2H), 1.30 (d, =6.4 Hz, 3H).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. washthe filtrate was washed with methanol (5×30 mL)
  3. concentrationconcentrated in vacuo
  4. customthe residue was purified by chromatography on silica gel (eluting with 10% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-1457538487044c2b895bf9f8594cbef6
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115151B2

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