HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acrylamide → 3-(4-Amino-3,5-dimethylphenyl)-2-propenenitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acrylamide | HCID 6579 | — |
| Reactant | Phosphorus oxychloride | HCID 24813 | — |
| Reactant | Tri-o-tolylphosphine | HCID 80271 | — |
| Reactant | 4-Bromo-2,6-xylidine | HCID 90549 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 3-(4-Amino-3,5-dimethylphenyl)-2-propenenitrile | HCID 57350233 | 67% |
Reaction Steps
The third route disclosed in WO 03/016306 involved reaction of 4-bromo-2,6-dimethylphenylamine with acrylamide in presence of palladium acetate, tris(2-methylphenyl)phosphine and N,N-diethylethanamine. The resulting amide was dehydrated using phosphoryl chloride to give 4-(2-cyanoethenyl)-2,6-dimethylphenylamine in a moderate yield of 67% without mentioning the E/Z ratio.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08952155B2 |
| Source dataset | uspto-grants-2015_02 |
| ORD ID | ord-6caf65c909424b25887d3bbd84f14953 |
| Source note | uspto-grants-2015_02 |