Nitric Acid → HCID 1736319, compound

HRID 1914784Notes

Reaction equation

HRID 1914784 reaction equation
[Cl:1][C:2]1[C:18]([OH:19])=[CH:17][C:5]2[C:6]([C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:10])=[CH:7][O:8][C:4]=2[C:3]=1[Cl:20].[N+]([O-])(O)=[O:22]>C(O)(=O)C>[C:9]([C:6]1[C:5]2[C:17](=[O:22])[C:18](=[O:19])[C:2]([Cl:1])=[C:3]([Cl:20])[C:4]=2[O:8][CH:7]=1)(=[O:10])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 23855137HCID 23855137, compound

Product 1

HCID 1736319HCID 1736319, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of compound 4 (100 mg, 0.32 mmol) in glacial acetic acid (2 mL) at room temperature was added nitric acid (0.1 mL, d 1.35) dropwise with vigorous stirring. The mixture was heated at 60° C. for 3 h, allowed to cool to room temperature, and poured over crushed ice. The resulting precipitate was filtered, dried, and recrystallized (CH2Cl2-pet. ether) to afford compound SKC-BF-09 (40 mg, 40%) as brick red solid. TLC Rf=0.5 (petroleum ether-EtOAc, 7:3); 1H NMR (CDCl3) δ 7.93 (s, 1H), 7.86 (d, J=6.9 Hz, 2H), 7.64 (app t, 1H), 7.50 (d, J=7.6 Hz, 2H); MS (ES) m/z 321 (M+H)+.

Workup

  1. temperatureto cool to room temperature
  2. additionpoured
  3. customover crushed ice
  4. filtrationThe resulting precipitate was filtered
  5. customdried
  6. customrecrystallized (CH2Cl2-pet. ether)
  7. customto afford compound SKC-BF-09 (40 mg, 40%) as brick red solid

Sources & evidence

ORD record
ord-59ba6fef9a6647aa846ad6c588216e12
Source dataset
uspto-grants-2013_12
Patent number
US08614237B2

Reaction notes

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