Nitric Acid → HCID 49820160, compound

HRID 1914787Notes

Reaction equation

HRID 1914787 reaction equation
Cl[C:2]1[C:7]2[C:8]([C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)=[O:12])=[CH:9][O:10][C:6]=2[CH:5]=[C:4]([Cl:21])[C:3]=1[OH:22].[N+]([O-])(O)=[O:24].O>C(O)(=O)C>[Cl:21][C:4]1[C:3](=[O:22])[C:2](=[O:24])[C:7]2[C:8]([C:11](=[O:12])[C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)=[CH:9][O:10][C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 56673617HCID 56673617, compound

Product 1

HCID 49820160HCID 49820160, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of compound 10d (100 mg, 0.29 mmol) in glacial acetic acid (1.5 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 30 min, allowed to cool to room temperature, and poured into cold water. The resulting precipitate was filtered and recrystallized (CH2Cl2-pet. ether) to furnish compound SKC-BF-04 (50 mg, 53%) as a red solid. TLC Rf=0.4 (petroleum ether-EtOAc, 7:3); 1H NMR (CDCl3) δ 7.86-7.80 (m, 3H), 7.54 (s, 1H), 6.95 (d, J=9.0 Hz, 2H), 3.88 (s, 3H); MS (ES) m/z 317 (M+H)+.

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe resulting precipitate was filtered
  3. customrecrystallized (CH2Cl2-pet. ether)
  4. customto furnish compound SKC-BF-04 (50 mg, 53%) as a red solid

Sources & evidence

ORD record
ord-4aaea69e28d140558ec9f543f8c5ce2a
Source dataset
uspto-grants-2013_12
Patent number
US08614237B2

Reaction notes

Loading…