Nitric Acid → HCID 19377779, compound

HRID 2210892Notes

Reaction equation

HRID 2210892 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([NH:6][C:7]2[CH:8]=[C:9]3[CH2:17][O:16][CH2:15][CH2:14][C:10]3=[N+:11]([O-:13])[CH:12]=2)=[N:2]1.C(Cl)(Cl)Cl.[N+:22]([O-])([OH:24])=[O:23]>>[O:1]1[CH:5]=[CH:4][C:3]([NH:6][C:7]2[C:8]([N+:22]([O-:24])=[O:23])=[C:9]3[CH2:17][O:16][CH2:15][CH2:14][C:10]3=[N+:11]([O-:13])[CH:12]=2)=[N:2]1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 6212ChloroformHCID 19377768HCID 19377768, compound

Product 1

HCID 19377779HCID 19377779, compoundYield 70%

Conditions

Temperature
55 °C

Procedure

A solution of 653 mg of Compound 5 obtained in the above step (1) as crystals in 3.2 ml of fuming nitric acid is stirred at 55° C. for 3 hours. The reaction mixture is chilled, poured onto ice water and shaken with chloroform. The extract is washed with water, aqueous disodium hydrogen phosphate and saturated saline in this order, dried over anhydrous magnesium sulfate and concentrated to remove the solvent. The resultant residue is washed with methanol to give 551 mg of the titled compound as light yellow crystals. Yield: 70% mp.: 174° to 176° C. (dec.)

Workup

  1. temperatureThe reaction mixture is chilled
  2. additionpoured onto ice water
  3. washThe extract is washed with water, aqueous disodium hydrogen phosphate and saturated saline in this order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto remove the solvent
  7. washThe resultant residue is washed with methanol

Sources & evidence

ORD record
ord-9c58b9647a254394b4b5d7c552461174
Source dataset
uspto-grants-1995_10
Patent number
US05461062

Reaction notes

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