Nitric Acid → 7-Fluoro-6-nitro-2H-1,4-benzoxazin-3(4H)-one

HRID 414636Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 414636
[F:1][C:2]1[CH:12]=[CH:11][C:5]2[NH:6][C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.[N+:13]([O-])([OH:15])=[O:14]>S(=O)(=O)(O)O>[F:1][C:2]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:5]2[NH:6][C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 137312957-fluoro-3,4-dihydro-2H-1,4-benzoxazin-3-one

Produkt 1

HCID 137312977-Fluoro-6-nitro-2H-1,4-benzoxazin-3(4H)-oneAusbeute 82,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

A solution of 7-fluoro-2H-1,4-benzoxazin-3(4H)-one (2.0 g) in 80% aqueous sulfuric acid (30 ml) was cooled to 0° to 5° C., and 60% nitric acid (1.6 g) was gradually added thereto at 0° to 5° C. The resultant mixture was stirred at the same temperature for 30 minutes and poured onto ice water. The precipitated crystals were collected by filtration, washed with water and dried to give 7-fluoro-6-nitro-2H-1,4-benzoxazin-3(4H)-one (2.1 g) as pale brown crystals. m.p., 205.9° C. 1H-NMR (CDCl3 +DMSO-D6) δ ppm: 3.2 (1H, broad), 4.62 (2H, s), 6.76 (1H, d, J=10 Hz), 7.6 (1H, d, J=6 Hz).

Aufarbeitung

  1. customat 0° to 5° C
  2. additionpoured onto ice water
  3. filtrationThe precipitated crystals were collected by filtration
  4. washwashed with water
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-83176ecb1f40492db285baea42410e0a
Quelldatensatz
uspto-grants-1988_12
Patentnummer
US04792605

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