Nitric Acid → HCID 9975520, compound

HRID 1106433Notes

Reaction equation

HRID 1106433 reaction equation
[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[C:7]([Br:18])[CH:8]=[CH:9][C:10]=2[NH:14][C:15](=[O:17])[CH3:16])[CH2:5]1)(=[O:3])[CH3:2].[N+:19]([O-])([OH:21])=[O:20]>FC(F)(F)C(O)=O.C(Cl)(Cl)Cl>[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[C:7]([Br:18])[CH:8]=[C:9]([N+:19]([O-:21])=[O:20])[C:10]=2[NH:14][C:15](=[O:17])[CH3:16])[CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 10358081HCID 10358081, compound

Product 1

HCID 9975520HCID 9975520, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The product from Example 21 (31 g) was dissolved in trifluoroacetic acid (450 mL). The solution was treated dropwise with 33 mL of fuming 90% nitric acid and stirred at room temperature. The reaction mixture was concentrated, the residue was dissolved in chloroform and then washed well with sodium bicarbonate solution. A solid formed, and was dissolved in 3 L chloroform and dried over magnesium sulfate. After evaporation, the residue was crystallized from ethyl acetate to give a white solid (19.32 g), and the filtrate concentrated to give an additional 16.3 g.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in chloroform
  3. washwashed well with sodium bicarbonate solution
  4. customA solid formed
  5. dry with materialdried over magnesium sulfate
  6. customAfter evaporation
  7. customthe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-27bd6f2ba32348e0aa79d4e12d950fe5
Source dataset
uspto-grants-2000_05
Patent number
US06057313

Reaction notes

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