Nitric Acid → HCID 46944248, compound

HRID 1914792Notes

Reaction equation

HRID 1914792 reaction equation
[Br:1][C:2]1[C:22]([OH:23])=[CH:21][C:5]2[C:6]([C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=3)=[O:10])=[CH:7][O:8][C:4]=2[C:3]=1[Br:24].[N+]([O-])(O)=[O:26].O.C(Cl)(Cl)Cl.CO>C(O)(=O)C>[Br:1][C:2]1[C:22](=[O:23])[C:21](=[O:26])[C:5]2[C:6]([C:9](=[O:10])[C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=3)=[CH:7][O:8][C:4]=2[C:3]=1[Br:24]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 21584188Chloroform methanolHCID 56676937HCID 56676937, compound

Product 1

HCID 46944248HCID 46944248, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of compound 14 (100 mg, 0.22 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 30 min, allowed to cool to room temperature, and poured into cold water. The resulting precipitate was filtered and recrystallized to obtain compound SKC-BF-12 (40 mg, 40%) as an orange solid. TLC Rf=0.7 (CHCl3-MeOH, 9:1); 1H NMR (CDCl3) δ 7.87 (s, 1H), 7.57 (app s, 1H), 7.37 (dd, J=8.4 Hz, 2.0 Hz, 1H), 6.84 (d, J=8.3, 1H), 3.95 (s, 6H); MS (ES) m/z 471 (M+H)+.

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe resulting precipitate was filtered
  3. customrecrystallized
  4. customto obtain compound SKC-BF-12 (40 mg, 40%) as an orange solid

Sources & evidence

ORD record
ord-8b8f1f45a5bf42b181f5c614417aa1f3
Source dataset
uspto-grants-2013_12
Patent number
US08614237B2

Reaction notes

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