HuagongsheHuagongshe Chemistry Print Report · For research reference only
N-Methylpropylamine → 5-Hydroxymethyl-N-methyl-isophthalamic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | N-Methylpropylamine | HCID 12315 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 3-(Ethoxycarbonyl)-5-(hydroxymethyl)benzoic acid | HCID 21085829 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 5-Hydroxymethyl-N-methyl-isophthalamic acid ethyl ester | HCID 68815250 | 47.7% |
Reaction Steps
Stir a solution of 5-hydroxymethyl-isophthalic acid monoethyl ester (1.9 g, 8.4 mmol), N-methylpropylamine (947 μl, 9.2 mmol), 1-hydroxybenzotriazole (1.24 g, 9.2 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.77 g, 9.2 mmol) in a mixture of dichloromethane (12 mL) and DMF (12 mL) at room temperature for 1.5 h. Concentrate and purify (silica gel chromatography, eluting with 50:50 ethyl acetate:hexanes) to give the title compound (950 mg, 40% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07585885B2 |
| Source dataset | uspto-grants-2009_09 |
| ORD ID | ord-ddf4451e79d54a589c18c27ec96cf54e |
| Source note | uspto-grants-2009_09 |