Nitric Acid → HCID 14771560, compound

HRID 329720Notes

Reaction equation

HRID 329720 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:14]([OH:16])=[O:15])[C:5]2[O:10][CH2:9][C:8](=[O:11])[N:7]([CH3:12])[C:6]=2[CH:13]=1.[N+:17]([O-])([OH:19])=[O:18]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:3]([N+:17]([O-:19])=[O:18])=[C:4]([C:14]([OH:16])=[O:15])[C:5]2[O:10][CH2:9][C:8](=[O:11])[N:7]([CH3:12])[C:6]=2[CH:13]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 147715626-Chloro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylic acid

Product 1

HCID 14771560HCID 14771560, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a solution of 60 g of 6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid in 450 ml of concentrated sulfuric acid with cooling below 0° C. is added dropwise a mixture of 11.6 ml of fuming nitric acid and 11.6 ml of concentrated sulfuric acid at a temperature below 5° C. The resultant solution is stirred under ice-cooling for 2.5 hours and poured into ice-cold water. The precipitated crystals are collected by filtration and recrystallized from ethanol to give 6-chloro-3,4-dihydro-4-methyl-7-nitro-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid, melting at 257° C. with decomposition.

Workup

  1. additionis added dropwise
  2. temperaturecooling for 2.5 hours
  3. additionpoured into ice-cold water
  4. filtrationThe precipitated crystals are collected by filtration
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-e24b6c04918e4b6ab02a5b45230e1142
Source dataset
uspto-grants-1990_01
Patent number
US04892872

Reaction notes

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