Nitric Acid → HCID 49820312, compound

HRID 1914794Notes

Reaction equation

HRID 1914794 reaction equation
[Cl:1][C:2]1[C:24]([OH:25])=[CH:23][C:5]2[C:6]([C:9]([C:11]3[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=3)=[O:10])=[CH:7][O:8][C:4]=2[C:3]=1[Cl:26].[N+]([O-])(O)=[O:28].O.C(Cl)(Cl)Cl.CO>C(O)(=O)C>[Cl:1][C:2]1[C:24](=[O:25])[C:23](=[O:28])[C:5]2[C:6]([C:9](=[O:10])[C:11]3[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=3)=[CH:7][O:8][C:4]=2[C:3]=1[Cl:26]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 21584188Chloroform methanolHCID 56670102HCID 56670102, compound

Product 1

HCID 49820312HCID 49820312, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of compound 22 (100 mg, 0.25 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, left to cool for 30 min, and poured into cold water. The resulting precipitate was filtered and recrystallized to afford compound SKC-BF-11 (50 mg, 49%) as an orange solid. TLC Rf=0.6 (CHCl3-MeOH, 9:1); 1H NMR (CDCl3) δ 7.90 (s, 1H), 7.13 (s, 2H), 3.95 (s, 3H), 3.88 (s, 6H); MS (ES) m/z 411 (M+H)+.

Workup

  1. waitleft
  2. temperatureto cool for 30 min
  3. filtrationThe resulting precipitate was filtered
  4. customrecrystallized
  5. customto afford compound SKC-BF-11 (50 mg, 49%) as an orange solid

Sources & evidence

ORD record
ord-74059381ae844d54b6720ac27cd8bb41
Source dataset
uspto-grants-2013_12
Patent number
US08614237B2

Reaction notes

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