HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 906187Generated: October 30, 2026
Isobutylamine → Ethyl 4-cyano-3-[(2-methylpropylamino)]benzoate
https://huagongshe.com/reaction/906187
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Isobutylamine | HCID 6558 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | Ethyl 3-bromo-4-cyanobenzoate | HCID 18374323 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | Ethyl 4-cyano-3-[(2-methylpropylamino)]benzoate | HCID 67405767 | 76.7% |
Reaction Steps
A mixture of ethyl 3-bromo-4-cyanobenzoate (500 mg, 2.08 mmol), 2-methylpropan-1-amine (250 μL, 4.16 mmol), Pd2(dba)3 (96 mg, 5 mol %), Xantphos (120 mg, 10 mol %) and potassium phosphate (959 mg, 4.16 mmol) in dioxane (10 mL) was stirred for overnight at 95° C. After cooling to room temperature the mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated followed by column chromatography (10% ethyl acetate in hexanes) to give ethyl 4-cyano-3-[(2-methylpropylamino)]benzoate (393 mg, 76.7%) as a yellow solid. 1MS (EI) for C14H18N2O2: 247.1 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08012956B2 |
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| Source dataset | uspto-grants-2011_09 |
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| ORD ID | ord-893de11e4b9e48e6a28b510f3b5248e1 |
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| Source note | uspto-grants-2011_09 |
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