HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → methyl 1H-indole-5-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | 1H-Indole-5-Carboxylic Acid | HCID 74280 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | methyl 1H-indole-5-carboxylate | HCID 2737635 | — |
Reaction Steps
A mixture of 5-carboxyindole (32.2 g, 0.2 mol), NaHCO3 (53.36 g, 0.64 mol), methyl iodide (122.22 g, 0.86 mol) in 60 mL of DMF were stirred at RT for 2 days. Water and EtOAc are added, and the organic layer was washed with bicarbonate solution, dried and concentrated to obtain 5-(methoxycarbonyl)indole. 1H NMR (DMSO) δ: 11.44 (s, 1H), 8.22 (s, 1H), 7.68 (d, J=8.4 Hz, 1H), 7.37˜7.47 (m, 2 H), 6.56 (d, J=2.0 Hz, 1H), 3.80 (s, 3H). MS (ESI) m/e (M+H+): 176.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08871759B2 |
| Source dataset | uspto-grants-2014_10 |
| ORD ID | ord-7b13bbd824cc4533b87415573fa00b36 |
| Source note | uspto-grants-2014_10 |