HuagongsheHuagongshe Chemistry Print Report · For research reference only
(3,4-Dimethoxyphenyl)acetic acid → 2-(3,4-dimethoxyphenyl)-N-methoxy-N-methylacetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (3,4-Dimethoxyphenyl)acetic acid | HCID 7139 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-(3,4-dimethoxyphenyl)-N-methoxy-N-methylacetamide | HCID 11218651 | 66.1% |
Reaction Steps
(3,4-Dimethoxyphenyl)acetic acid (13.0 g, 66.4 mmol) was suspended in anhydrous CH2Cl2 followed by addition of EDCI (15.3 g, 79.7 mmol), HOBt (20.6 g, 152 mmol), triethylamine (8.06 g, 79.7 mmol), and N,O-dimethylhydroxylamine hydrochloride (6.48 g, 66.4 mmol). The reaction was stirred 3 days at ambient temperature after which the solvent was evaporated at reduced pressure. The residue was partitioned between EtOAc and water. The organic layer was washed with aq. HCl, sat NaHCO3, brine, dried (Na2SO4), and concentrated in vacuo to give 10.5 g (66%) of N-methyl-N-methoxy-(3,4-dimethoxyphenyl)acetamide as a pale brown oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06030969 |
| Source dataset | uspto-grants-2000_02 |
| ORD ID | ord-26f784be0e59469797b42eadcca21f48 |
| Source note | uspto-grants-2000_02 |