Nitric Acid → HCID 49820161, compound

HRID 1914789Notes

Reaction equation

HRID 1914789 reaction equation
[Cl:1][C:2]1[C:20]([OH:21])=[CH:19][C:5]2[C:6]([C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[O:10])=[CH:7][O:8][C:4]=2[C:3]=1[Cl:22].[N+]([O-])(O)=[O:24].O.C(Cl)(Cl)Cl.CO>C(O)(=O)C>[Cl:1][C:2]1[C:20](=[O:21])[C:19](=[O:24])[C:5]2[C:6]([C:9](=[O:10])[C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[CH:7][O:8][C:4]=2[C:3]=1[Cl:22]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 21584188Chloroform methanolHCID 56680249HCID 56680249, compound

Product 1

HCID 49820161HCID 49820161, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of compound 10f (100 mg, 0.29 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 hr, allowed to cool for 30 min, and poured into cold water. The resulting precipitate was filtered, washed with water, and dried under high vacuum to afford compound SKC-BF-05 (45 mg, 42%) as an orange solid. TLC Rf=0.7 (CHCl3-MeOH, 9:1); 1H NMR (CDCl3) δ 7.89 (s, 1H), 7.85 (d, J=9.0 Hz, 2H), 6.95 (d, J=9.0 Hz, 2H), 3.89 (s, 3H); MS (ES) m/z 351 (M+H)+.

Workup

  1. temperatureto cool for 30 min
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. customdried under high vacuum
  5. customto afford compound

Sources & evidence

ORD record
ord-fdd6a2ec3c814fa7a1e50c8889fc1d22
Source dataset
uspto-grants-2013_12
Patent number
US08614237B2

Reaction notes

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