Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethoxyethylamine | HCID 66970 | — |
| Reactant | Benzoic acid, 2-fluoro-, ethyl ester | HCID 67953 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 70873910 | HCID 70873910 | — |
Reaction Steps
To a stirred solution of commercially available 2-Fluoro-benzoic acid ethyl ester (1 g, 6.01 mmol) and 2-Ethoxy-ethylamine (0.500 g, 2.97 mmole) in dry N,N′dimethylformamide (10 mL) in a screw cap vial was added diisopropylethylamine (1.1 eq, 0.223 g, 3.27 mmole, 1.1 mL). The resulting solution was heated to 120° C. for 4 hours. Reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate (25 mL×3). Combined organic phase was washed consecutively with water, brine before drying over sodium sulfate. Organic phase was evaporated and the residue was purified by flash chromatography to afford 2-(2-Ethoxy-ethylamino)-benzoic acid ethyl ester as a clear liquid (0.493 g, 70%, LCMS calc M+H 238, obs M+H 238).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09133164B2 |
|---|
| Source dataset | uspto-grants-2015_09 |
|---|
| ORD ID | ord-91d6690ea3bc4e67b839d863a8e3c368 |
|---|
| Source note | uspto-grants-2015_09 |
|---|