Potassium Hydroxide → HCID 46199201, compound

HRID 2046026Notes

Reaction equation

HRID 2046026 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]4[O:25][C:24]([CH:26]=[O:27])=[CH:23][C:22]=4[CH:28]=3)[N:14]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].[OH-:29].[K+]>CCO.[N+]([O-])([O-])=O.[Ag+]>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]4[O:25][C:24]([C:26]([OH:29])=[O:27])=[CH:23][C:22]=4[CH:28]=3)[N:14]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86660602HCID 86660602, compound

Product 1

HCID 46199201HCID 46199201, compoundYield 12.8%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of the product of Step E (0.009 g; 0.024 mmol) and AgNO3 (0.06 g; 0.14 mmol) in EtOH (0.2 ml) H2O (0.1 ml) was added at room temperature, followed by 10% KOH (0.1 ml). The resulting black suspension was stirred for 1 h at ˜50° C. and cooled to room temperature and filtered. The insoluble material was washed with H2O (2×0.2 ml). The combined filtrates were acidified to pH=1 with HCl and the product was taken up by extraction with EtOAc (2×5 ml). The organic phase was washed with brine, dried over anhydrous MgSO4, filtered and filtrate evaporated to dryness. The residue was purified by FCC (SiO2, CH2Cl2/acetic acid (AcOH) 98/2) to give the title compound (0.00012 g; 12.8%), as a creamy solid. 1H-NMR (CDCl3+CD3OD) 8.48 (s, 1H); 8.22 (m, 1H); 7.77 (m, 1H); 7.64-7.66 (m, 2H); 7.58 (s, 1H); 6.96 (d, 1H, J=6 Hz); 4.19 (m, 4H); 1.4-1.54 (m, 6H).

Workup

  1. additionwas added at room temperature
  2. temperaturecooled to room temperature
  3. filtrationfiltered
  4. washThe insoluble material was washed with H2O (2×0.2 ml)
  5. extractionthe product was taken up by extraction with EtOAc (2×5 ml)
  6. washThe organic phase was washed with brine
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. customfiltrate evaporated to dryness
  10. customThe residue was purified by FCC (SiO2, CH2Cl2/acetic acid (AcOH) 98/2)

Sources & evidence

ORD record
ord-719821e485da46978e7898cab0c83935
Source dataset
uspto-grants-2013_11
Patent number
US08592399B2

Reaction notes

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