Nitric Acid → 5-Methyl-6-nitro-1H-benzo[d][1,3]oxazine-2,4-dione

HRID 1840861

Reaktionsgleichung

[CH3:1][C:2]1[C:7]2[C:8](=[O:13])[O:9][C:10](=[O:12])[NH:11][C:6]=2[CH:5]=[CH:4][CH:3]=1.[N+:14]([O-])([OH:16])=[O:15]>OS(O)(=O)=O>[CH3:1][C:2]1[C:7]2[C:8](=[O:13])[O:9][C:10](=[O:12])[NH:11][C:6]=2[CH:5]=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of 5-methyl-4H-3,1-benzoxazin-2,4-dione (20 g, 113 mmol) in 150 mL of concentrated H2SO4, cooled to −15° C., was added 7.83 g of 90% w/w HNO3 (in 30 mL of conc. H2SO4) dropwise at such a rate to keep the internal temperature below 5° C. After the addition was complete, the reaction was stirred at 0° C. for an additional 20 minutes then quenched by pouring the reaction mixture over crushed ice. Following further dilution with water, the resulting precipitate was filtered, washed with water, resuspended in water then filtered and washed again with water affording 15.1 g (60%) of 5-methyl-6-nitro-4H-3,1-benzoxazin-2,4-dione, after drying: Anal. Calc'd. for C9H6N2O5: C, 48.66; H, 2.72; N, 12.61. Found: C, 48.19; H, 2.54; N, 12.51.

Aufarbeitung

customthe internal temperature below 5° C
additionAfter the addition
customthen quenched
additionby pouring the reaction mixture
customover crushed ice
filtrationthe resulting precipitate was filtered
washwashed with water
filtrationthen filtered
washwashed again with water affording 15.1 g (60%) of 5-methyl-6-nitro-4H-3,1-benzoxazin-2,4-dione
customafter drying

Quellen und Nachweise

ORD-Eintrag: ord-0b26b609e1d14b6390bb1269a4228386
Quelldatensatz: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06683077B2

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