Nitric Acid → HCID 49820935, compound

HRID 1914798Notes

Reaction equation

HRID 1914798 reaction equation
[OH:1][C:2]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:5]2[O:6][CH:7]=[C:8]([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])[C:4]=2[CH:3]=1.[N+]([O-])(O)=[O:30].O.C(Cl)(Cl)Cl.CO>C(O)(=O)C>[CH3:22][O:21][C:13]1[CH:12]=[C:11]([CH:16]=[C:15]([O:17][CH3:18])[C:14]=1[O:19][CH3:20])[C:9]([C:8]1[C:4]2[C:3](=[O:30])[C:2](=[O:1])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:5]=2[O:6][CH:7]=1)=[O:10]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 21584188Chloroform methanolHCID 66645277HCID 66645277, compound

Product 1

HCID 49820935HCID 49820935, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
45 °C

Procedure

To a suspension of compound 25 (250 mg, 0.66 mmol) in glacial acetic acid (1.5 mL) at room temperature was added nitric acid (0.4 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 furnish compound SKC-NF-03 (100 mg, 38%) as a yellow solid. TLC Rf=0.6 (CHCl3-MeOH, 9.5:0.5); 1H NMR (CDCl3) δ 8.15 (d, J=7.6 Hz, 1H), 7.84-7.80 (m, 2H), 7.73 (app t, 1H), 7.55 (app t, 1H), 7.18 (s, 2H), 3.95 (s, 3H), 3.87 (s, 6H); MS (ES) m/z 393 (M+H)+.

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe resulting precipitate was filtered
  3. customrecrystallized
  4. customto furnish compound SKC-NF-03 (100 mg, 38%) as a yellow solid

Sources & evidence

ORD record
ord-3cb485bbe8c248b292524c287b833d7c
Source dataset
uspto-grants-2013_12
Patent number
US08614237B2

Reaction notes

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