Nitric Acid → HCID 14771561, compound

HRID 329721Notes

Reaction equation

HRID 329721 reaction equation
[CH3:1][N:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([C:12]([OH:14])=[O:13])[C:6]=2[O:5][CH2:4][C:3]1=[O:15].[N+:16]([O-])([OH:18])=[O:17]>S(=O)(=O)(O)O>[CH3:1][N:2]1[C:7]2[CH:8]=[C:9]([N+:16]([O-:18])=[O:17])[CH:10]=[C:11]([C:12]([OH:14])=[O:13])[C:6]=2[O:5][CH2:4][C:3]1=[O:15]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 14802113HCID 14802113, compound

Product 1

HCID 14771561HCID 14771561, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a solution of 85.5 g of 3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid in 222 ml of concentrated sulfuric acid with cooling to -8° C. is added dropwise with stirring a mixture of 20.7 ml of fuming nitric acid (d 1.50) and 20.7 ml of concentrated sulfuric acid at a temperature below 2° C. over about 30 minutes, and the solution further stirred under cooling. The resultant solution is poured into ice-cold water with stirring. The precipitated crystals are collected by filtration, washed with water and dried to give 99 g of 3,4-dihydro-4-methyl-6-nitro-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid, melting at 256°-259° C. with decomposition.

Workup

  1. additionis added dropwise
  2. stirringthe solution further stirred
  3. temperatureunder cooling
  4. stirringwith stirring
  5. filtrationThe precipitated crystals are collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-1400f9909759411583e99233b5dad8fd
Source dataset
uspto-grants-1990_01
Patent number
US04892872

Reaction notes

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