Nitric Acid → HCID 14988424, compound

HRID 1198467Notes

Reaction equation

HRID 1198467 reaction equation
[O:1]1[C:6]2=[CH:7][CH:8]=[CH:9][C:10]3[C:11](=[O:14])[C:12](=[O:13])[N:4]([C:5]=32)[CH2:3][CH2:2]1.[N+:15]([O-])([OH:17])=[O:16]>C(OC(=O)C)(=O)C>[N+:15]([C:8]1[CH:7]=[C:6]2[O:1][CH2:2][CH2:3][N:4]3[C:12](=[O:13])[C:11](=[O:14])[C:10]([CH:9]=1)=[C:5]23)([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 11063189HCID 11063189, compound

Product 1

HCID 14988424HCID 14988424, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazine-5,6-dione (33.1 g) in acetic acid-acetic anhydride (200 ml, 1:1) under ice-cooling was added fuming nitric acid (9.4 ml) dropwise. The mixture was stirred for 0.5 hours at the same temperature (0° C.) and for an hour at room temperature. The reaction mixture was poured into ice water (500 ml) and the resultant precipitate was collected by filtration. This precipitate was washed with water and dried to give 26.9 g (65.5%) of the title compound. The filtrate was extracted with chloroform, washed with water, saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride solution successively and then dried over anhydrous sodium sulfate. Evaporation of chloroform further afforded 2.9 g of the title compound. This compound was recrystallized from acetonitrile to give yellow needles, mp 230°-232° C.

Workup

  1. filtrationthe resultant precipitate was collected by filtration
  2. washThis precipitate was washed with water
  3. customdried

Sources & evidence

ORD record
ord-bbad8efe79104ec29cc0bf9fe6b0c577
Source dataset
uspto-grants-1994_01
Patent number
US05281600

Reaction notes

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