Nitric Acid → HCID 1614226, compound

HRID 1914795Notes

Reaction equation

HRID 1914795 reaction equation
[OH:1][C:2]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:5]2[O:6][CH:7]=[C:8]([C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[O:10])[C:4]=2[CH:3]=1.[N+]([O-])(O)=[O:26].O.C(Cl)Cl.CO>C(O)(=O)C>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]([C:8]2[C:4]3[C:3](=[O:26])[C:2](=[O:1])[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:5]=3[O:6][CH:7]=2)=[O:10])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 746633HCID 746633, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 1614226HCID 1614226, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
45 °C

Procedure

To a suspension of compound 23 (100 mg, 0.31 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 then heated at 45° C. for 30 min, left to cool for 30 min, and poured into cold water. The resulting precipitate was filtered and recrystallized to obtain compound SKC-NF-01 (45 mg, 43%) as an orange solid. TLC Rf=0.4 (CH2Cl2-MeOH, 9:1); 1H NMR (CDCl3) δ 8.13 (d, J=7.0 Hz, 1H), 7.90 (app d, 2H), 7.86-7.82 (m, 2H), 7.72 (app t, 1H), 7.54 (app t, 1H), 6.94 (m, 2H), 3.88 (s, 3H); MS (ES) m/z 333 (M+H)+.

Workup

  1. waitleft
  2. temperatureto cool for 30 min
  3. filtrationThe resulting precipitate was filtered
  4. customrecrystallized
  5. customto obtain compound SKC-NF-01 (45 mg, 43%) as an orange solid

Sources & evidence

ORD record
ord-d400ce74cba244349d67274e114bb9be
Source dataset
uspto-grants-2013_12
Patent number
US08614237B2

Reaction notes

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