Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Chlorobutyryl chloride | HCID 78370 | — |
| Reactant | HCID 45089063 | HCID 45089063 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 69356535 | HCID 69356535 | 115% |
Reaction Steps
3-Amino-5-ethoxy-benzoic acid methyl ester (D49) (4.0 g, 20.5 mmol, 1 equiv) was suspended in CH2Cl2 (40 ml) and treated at room temperature with NEt3 (2.32 g, 23 mmol, 1.1 equiv). The resulting solution was cooled to 0° C. and 4-chlorobutyryl chloride (3.1 g, 22 mmol, 1.1 equiv) was added dropwise. The resulting mixture was stirred at 0° C. for 3 h then allowed to warm to room temperature. The solution was washed with 2N aqueous HCl solution, dried over MgSO4 and concentrated in vacuo to give of 3-(4-chloro-butanoylamino)-5-ethoxy-benzoic acid methyl ester (D51) (7.0 g, 115%) as a brown oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07253198B2 |
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| Source dataset | uspto-grants-2007_08 |
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| ORD ID | ord-6f6120a78ea842cea07d4ef42945bac6 |
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| Source note | uspto-grants-2007_08 |
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