HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1745855Generated: October 31, 2026
2-Amino-5-chlorobenzoic acid → 2-amino-5-chloro-N-methoxy-N-methylbenzamide
https://huagongshe.com/reaction/1745855
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2-Amino-5-chlorobenzoic acid | HCID 12476 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-amino-5-chloro-N-methoxy-N-methylbenzamide | HCID 22226605 | 60% |
Reaction Steps
A solution of 2-amino-5-chlorobenzoic acid (5.0 g, 29.1 mmol), N,O-dimethylhydroxylamine hydrochloride (3.1 g, 32.0 mmol), and HOBt (3.9 g, 29.1 mmol) in CH2Cl2 (100 mL) was cooled to 0° C. and treated with EDCI (17.3 g, 87.3 mmol). The reaction was stirred at 25° C. for 12 h, diluted with H2O, and extracted with EtOAc. The organics were dried (Na2SO4), filtered, and concentrated. Chromatography (SiO2, 1:1 Hex/EtOAc) gave 8 (3.7 g, 60%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07019141B2 |
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| Source dataset | uspto-grants-2006_03 |
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| ORD ID | ord-97bec5ec9f1340ea9cc805b83e81ad9b |
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| Source note | uspto-grants-2006_03 |
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