Nitric Acid → HCID 49820934, compound

HRID 1914797Notes

Reaction equation

HRID 1914797 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:13]2[C:14]3[CH:25]=[C:24]([OH:26])[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:15]=3[O:16][CH:17]=2)=[O:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[N+]([O-])(O)=[O:28].O.C(Cl)(Cl)Cl.CO>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])[C:11]([C:13]1[C:14]2[C:25](=[O:28])[C:24](=[O:26])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:15]=2[O:16][CH:17]=1)=[O:12]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 21584188Chloroform methanolHCID 66647049HCID 66647049, compound

Product 1

HCID 49820934HCID 49820934, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
45 °C

Procedure

To a suspension of compound 24 (100 mg, 0.28 mmol) in glacial acetic acid (1.5 mL) at room temperature was added nitric acid (0.2 mL, d 1.35) dropwise with vigorous stirring. The mixture was heated at 45° C. for 30 min, allowed to cool to room temperature, and poured into cold water. The resulting precipitate was filtered and recrystallized to afford compound SKC-NF-02 (45 mg, 43%) as an orange solid. TLC Rf=0.4 (CHCl3-MeOH, 9:1); 1H NMR (CDCl3) δ 8.13 (d, J=7.0 Hz, 1H), 7.81 (m, 2H), 7.74 (app t, 1H), 7.61 (app s, 1H), 7.55 (app t, 1H), 7.43 (dd, J=8.4 Hz, 2.1 Hz, 1H), 6.85 (d, J=8.3 Hz, 1H), 3.96 (s, 6H); MS (ES) m/z 363 (M+H)+.

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe resulting precipitate was filtered
  3. customrecrystallized
  4. customto afford compound SKC-NF-02 (45 mg, 43%) as an orange solid

Sources & evidence

ORD record
ord-3955dac67f1c4c488de2dea755a6c6f9
Source dataset
uspto-grants-2013_12
Patent number
US08614237B2

Reaction notes

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