HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 531899Generated: October 25, 2026
Methyl Anthranilate → methyl 2-(9H-carbazol-1-ylamino)benzoate
https://huagongshe.com/reaction/531899
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl Anthranilate | HCID 8635 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 1-Bromo-9H-carbazole | HCID 11230335 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | methyl 2-(9H-carbazol-1-ylamino)benzoate | HCID 68242730 | — |
Reaction Steps
35.51 g (234.9 mmol) of methyl anthranilate are dissolved in 500 ml of toluene and degassed well. 52 g (213 mmol) of 1-bromocarbazole, 2.1 g (10.7 mmol) of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, 1.19 g (5.34 mmol) of Pd(OAc)2 and 76.5 g (234.9 mmol) of Cs2CO3 are added, and the mixture is then degassed and stirred at 100° C. under a protective-gas atmosphere for 24 h. The solids are subsequently filtered off via Celite, and the organic phase is washed with water, dried over MgSO4 and evaporated. The crude product is washed by stirring with hot heptane, giving 57.4 g (108 mmol), 86% of theory, purity according to HPLC 86%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09356243B2 |
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| Source dataset | uspto-grants-2016_05 |
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| ORD ID | ord-de53838ceb6f4bbcabb63ac118599e64 |
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| Source note | uspto-grants-2016_05 |
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