Sulfuric Acid → HCID 66664925, compound

HRID 1057217Notes

Reaction equation

HRID 1057217 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]2[C:4]=1[C:5](=[O:16])[CH:6]=[CH:7][C:8]2=[O:15].[CH3:17][NH2:18].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].S(=O)(=O)(O)O.[Cl-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>CO.O>[CH3:17][NH:18][C:6]1[C:5](=[O:16])[C:4]2[C:9]([C:8](=[O:15])[CH:7]=1)=[C:10]([O:13][CH3:14])[CH:11]=[CH:12][C:3]=2[O:2][CH3:1]

Participants

9

Reactant 6

HCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 6329MethylamineHCID 24436Sodium SulfateHCID 25408Sodium DichromateHCID 3343611,4-Naphthalenedione, 5,8-dimethoxy-

Product 1

HCID 66664925HCID 66664925, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

0.45 mM 5,8-dimethoxy-1,4-naphthoquinone (4) which had been prepared above was dissolved in 30 ml of methanol in 100 ml one-neck round flask and then, 0.687 mmol methylamine was added thereto and stirred at room temperature for 3 hours 0.64 mM sodium dichromate and 0.18 mM sulfuric acid dissolved in water were slowly dropped to the reaction mixture and stirred at room temperature for 3 minutes. Then, 50 ml of saturated sodium chloride was added to the reaction mixture, followed by extraction three times with 50 ml of chloroform and obtained organic layers were gathered and dehydrated with anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was subjected to silicagel column chromatography, thereby producing 2-methylamino-5,8-dimethoxy-1,4-naphthoquinone that was reddish brown. The yield and properties of the synthesized compound are as follows.

Workup

  1. additionwere slowly dropped to the reaction mixture
  2. extractionfollowed by extraction three times with 50 ml of chloroform
  3. customobtained organic layers
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe yield

Sources & evidence

ORD record
ord-f7b7233680814e57873755d1e7a00aaa
Source dataset
uspto-grants-2016_07
Patent number
US09400281B2

Reaction notes

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