Nitric Acid → HCID 178504978, compound

HRID 1031688Notes

Reaction equation

HRID 1031688 reaction equation
[OH:1][C:2]1[O:3][C:4]2[CH:12]=[C:11]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[C:10]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:9][C:5]=2[C:6](=[O:8])[CH:7]=1.[N+:25]([O-])([OH:27])=[O:26]>C(O)(=O)C>[OH:1][C:2]1[O:3][C:4]2[CH:12]=[C:11]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[C:10]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:9][C:5]=2[C:6](=[O:8])[C:7]=1[N+:25]([O-:27])=[O:26]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 178504976HCID 178504976, compound

Product 1

HCID 178504978HCID 178504978, compoundYield 20.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3.47 g of 2-hydroxy-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one was suspended in 50 ml of acetic acid. Thereto was added 1.67 ml of concentrated nitric acid (specific gravity: 1.38). The mixture was stirred for 20 minutes at 100°-110° C. The reaction mixture was introduced into 300 ml of ice water. The resulting crystal was collected by filtration, washed with water, and recrystallized from acetonitrile to obtain 800 mg (yield: 20.4%) of 2-hydroxy-7-methylsulfonylamino-3-nitro-6-phenoxy-4H-1-benzopyran-4-one having a melting point of 228°-230° C. (decomposed).

Workup

  1. filtrationThe resulting crystal was collected by filtration
  2. washwashed with water
  3. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-2256d991f70f426db08b8200656c3522
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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