1,4-Naphthoquinone → HCID 15052363, compound

HRID 2165857Notes

Reaction equation

HRID 2165857 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[C:11](=[O:12])[CH:10]=[CH:9][C:7](=[O:8])[C:5]=2[CH:6]=1.[O:13]=[C:14]([CH3:20])[CH2:15][CH2:16]C(O)=O.S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+]>C(#N)C.[N+]([O-])([O-])=O.[Ag+]>[O:8]=[C:7]([CH3:9])[CH2:5][CH2:4][C:9]1[C:7](=[O:8])[C:5]2[C:4]([C:11](=[O:12])[C:10]=1[CH2:16][CH2:15][C:14](=[O:13])[CH3:20])=[CH:3][CH:2]=[CH:1][CH:6]=2

Participants

6

Reactant 3

HCID 85301,4-NaphthoquinoneHCID 11579Levulinic AcidHCID 62648Ammonium Persulfate

Product 1

HCID 15052363HCID 15052363, compound

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 6342AcetonitrileSolvent

Procedure

Naphthoquinone (3.12 g, 20 mmol), 4-oxopentanoic acid (13.9 g, 120 mmol) and silver nitrate (2.0 g, 11.8 mmole) are combined in 30% aqueous acetonitrile at 65° C. A solution of ammonium peroxydisulfate (12.0 g, 52.6 mmole) is added dropwise over 30 minutes while the stirred mixture is maintained at 65°-75° C. On cooling, the mixture is extracted with diethyl ether (300 ml). The extract is then washed with water (3×50 ml), 5% NaHCO3 (2×50 ml) and brine (50 ml) and dried over MgSO4. After filtration through active carbon, the ether solution is evaporated to give crude 2,3-bis(3-oxobutyl)-1,4-naphthoquinone which is recrystallized from aqueous ethanol to give 1.45 g product, mp 110°-112° C. This 2,3-bis(3-oxobutyl)-1,4-naphthoquinone (0.456 g, 1.53 mmole), aminoguanidine hydrochloride (0.46 g, 4.3 mmole) and a drop of concentrated HCl are combined in 5 ml of 90% ethanol and heated at reflux for 3 hours. On cooling, 2,3-bis(3-(2-amidinohydrazono)butyl)-1,4-naphthoquinone crystallizes from the reaction mixture, and recrystallization from ethanol gives 400 mg product, mp 181°-183° C.

Workup

  1. temperatureis maintained at 65°-75° C
  2. temperatureOn cooling
  3. extractionthe mixture is extracted with diethyl ether (300 ml)
  4. washThe extract is then washed with water (3×50 ml), 5% NaHCO3 (2×50 ml) and brine (50 ml)
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration through active carbon
  7. customthe ether solution is evaporated

Sources & evidence

ORD record
ord-4a45cd0d10c2407b8c2e627eab3d7549
Source dataset
uspto-grants-1990_07
Patent number
US04942170

Reaction notes

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