Ethanol → HCID 9954251, compound

HRID 496360Notes

Reaction equation

HRID 496360 reaction equation
[N+](=[CH:3][C:4](C=[N+]=[N-])=O)=[N-].[CH3:9][O:10][C:11]1[C:12](=[O:33])[C:13]([CH3:32])=[C:14]([CH2:20][C:21]2[CH:26]=[CH:25][C:24](CCC(O)=O)=[CH:23][CH:22]=2)[C:15](=[O:19])[C:16]=1[O:17][CH3:18].[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1.[CH2:40]([OH:42])[CH3:41]>[N+]([O-])([O-])=O.[Ag+]>[CH3:9][O:10][C:11]1[C:12](=[O:33])[C:13]([CH3:32])=[C:14]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:3][CH2:4][CH2:41][C:40]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[O:42])=[CH:23][CH:22]=2)[C:15](=[O:19])[C:16]=1[O:17][CH3:18]

Participants

5

Reactant 3

HCID 702EthanolHCID 8083MorpholineHCID 131724365HCID 131724365, compound

Product 1

HCID 9954251HCID 9954251, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 24470Silver NitrateCatalyst

Procedure

3-(4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-ylmethyl)phenyl]propionic acid diazomethyl ketone (70 mg, 0.20 mmol) obtained in Step 1 of Method B of Example 26 was dissolved in dry ethanol (5 ml), to which were added silver nitrate (34 mg, 0.20 mmol) and morpholine (0.090 ml, 1.0 mmol), and the mixture was heated to reflux for 20 minutes. The reaction mixture was filtered and the solid was washed with ethanol. The filtrate and the wash solution were combined and the solvent was distilled off, the resulting residue was purified by a silica gel column chromatography (hexane:ethyl acetate=1:3) to yield the title compound (42 mg, 0.098 mmol, yield 49%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 20 minutes
  3. filtrationThe reaction mixture was filtered
  4. washthe solid was washed with ethanol
  5. distillationthe solvent was distilled off
  6. customthe resulting residue was purified by a silica gel column chromatography (hexane:ethyl acetate=1:3)

Sources & evidence

ORD record
ord-708c29a1787041fd90deb18f992581f5
Source dataset
uspto-grants-2005_09
Patent number
US06943196B1

Reaction notes

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