Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methyl Anthranilate | HCID 8635 | — |
| Reactant | 4-Bromo-3-methylbenzoyl chloride | HCID 7021534 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 67352936 | HCID 67352936 | 99.4% |
Reaction Steps
To 2-amino-benzoic acid methyl ester (3.1 g) in dichloromethane (31 mL) under slight cooling was added 3-methyl-4-bromobenzoyl chloride ([21900-25-4], 4.8 g) followed by a triethylamine (3.15 mL). The temperature of the solution was kept below 40° C. and the reaction mixture was then stirred at room temperature for an hour. After such time, additional dichloromethane was added (50 mL) and the reaction mixture was washed with water. The aqueous phase was further extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (heptane-ethyl acetate: 0-50%) to yield 2-(4-bromo-3-methyl-benzoylamino)-benzoic acid methyl ester (7.1 g). MS (m/e): 348.3 (M+H+, 100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07989657B2 |
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| Source dataset | uspto-grants-2011_08 |
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| ORD ID | ord-9a6357187e1445a391df88b345156a6b |
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| Source note | uspto-grants-2011_08 |
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