Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | Sodium Chloride | HCID 5234 | — |
| Reactant | Methylamine | HCID 6329 | — |
| Reactant | Sodium Sulfate | HCID 24436 | — |
| Reactant | Sodium Dichromate | HCID 25408 | — |
| Reactant | 1,4-Naphthalenedione, 5,8-dimethoxy- | HCID 334361 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 66664925 | HCID 66664925 | — |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09400281B2 |
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| Source dataset | uspto-grants-2016_07 |
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| ORD ID | ord-f7b7233680814e57873755d1e7a00aaa |
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| Source note | uspto-grants-2016_07 |
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