HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Anhydride → 2,3-Dihydromelatonin
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Anhydride | HCID 7918 | — |
| Reactant | Ethyl chloroformate | HCID 10928 | — |
| Reactant | 2,3-Dihydromelatonin | HCID 10130872 | — |
| Reactant | N-[2-(1-acetyl-5-methoxyindolin-3-yl)ethyl]acetamide | HCID 23283701 | — |
| Reactant | N-[2-(1-trifluoromethanesulphonyl-5-methoxyindolin-3-yl)ethyl]diacetamide | HCID 69944386 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 2,3-Dihydromelatonin | HCID 10130872 | — |
| Product | N-[2-(1-benzyloxycarbonyl-5-methoxyindolin-3-yl)ethyl]acetamide | HCID 23283708 | — |
Reaction Steps
N-[2-(5-Methoxyindolin-3-yl)ethyl]acetamide is prepared by the method described for the synthesis of N-[2-(1-acetyl-5-methoxyindolin-3-yl)ethyl]acetamide. The intermediate N-[2-(1-benzyloxycarbonyl-5-methoxyindolin-3-yl) ethyl]acetamide is prepared by reacting the N-[2-(5-methoxyindolin-3-yl)ethyl]acetamide with ethyl chloroformate in dichloromethane at 0° C. in the presence of triethylamine. The final acylation is carried out with acetic anhydride in refluxing toluene for 24 h, and allows N-[2-(1-trifluoromethanesulphonyl-5-methoxyindolin-3-yl)ethyl]diacetamide to be obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06004991 |
| Source dataset | uspto-grants-1999_12 |
| ORD ID | ord-83103320bbf24345acc760cdf3f20146 |
| Source note | uspto-grants-1999_12 |