Hydrochloric Acid → HCID 178440875, compound

HRID 1885723Notes

Reaction equation

HRID 1885723 reaction equation
O=[C:2]([CH3:22])[CH2:3][CH2:4][C:5]1[C:6](=[O:21])[C:7]2[C:12]([C:13](=[O:20])[C:14]=1[CH2:15][CH2:16][C:17](=O)[CH3:18])=[CH:11][CH:10]=[CH:9][CH:8]=2.[C:23]([NH:26][NH2:27])([NH2:25])=[NH:24].[ClH:28].Cl>C(O)C>[ClH:28].[ClH:28].[C:23]([NH:26][N:27]=[C:2]([CH3:22])[CH2:3][CH2:4][C:5]1[C:6](=[O:21])[C:7]2[C:12]([C:13](=[O:20])[C:14]=1[CH2:15][CH2:16][C:17](=[N:27][NH:26][C:23](=[NH:24])[NH2:25])[CH3:18])=[CH:11][CH:10]=[CH:9][CH:8]=2)(=[NH:25])[NH2:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 15052363HCID 15052363, compoundHCID 178418668HCID 178418668, compound

Product 1

HCID 178440875HCID 178440875, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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. temperatureheated
  2. temperatureat reflux for 3 hours
  3. temperatureOn cooling
  4. custom2,3-bis(3-(2-amidinohydrazono)butyl)-1,4-naphthoquinone crystallizes from the reaction mixture, and recrystallization from ethanol

Sources & evidence

ORD record
ord-3d08ec7386704e33b682bf36681ec656
Source dataset
uspto-grants-1992_09
Patent number
US05145975

Reaction notes

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