HuagongsheHuagongshe Chemistry Print Report · For research reference only
5-Methylindole → 5-Methylindoline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 5-Methylindole | HCID 11978 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | 5-methoxy-2,3-dihydro-1H-indole | HCID 10701974 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Product | 5-Methylindoline | HCID 14023679 | 99% |
Reaction Steps
5-Methylindoline was prepared from 5-methylindole using the procedure described for the preparation of 5-methoxyindoline. 5-Methylindole (11 g, 0.0835 mol) in glacial acetic acid (150 mL) in a 1 L 3-necked flask was reduced at 10-15° C. with sodium cyanoborohydride (15.8 g, 0.251 mol). Extraction with ethyl acetate provided 5-methylindoline (11 g, 0.0832 mol, 99% yield) as a thick oil which was used without further purification. The structure was corroborated by NMR spectroscopy.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07704667B2 |
| Source dataset | uspto-grants-2010_04 |
| ORD ID | ord-d01d4c3cbc214279923b9c09f839446b |
| Source note | uspto-grants-2010_04 |