HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl propiolate → 6-Hydroxy-2-methylnicotinonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl propiolate | HCID 13536 | — |
| Reactant | 1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) | HCID 24670 | — |
| Reactant | 3-Aminocrotonitrile | HCID 5324720 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 6-Hydroxy-2-methylnicotinonitrile | HCID 11378516 | — |
Reaction Steps
A solution of (E)-3-amino-but-2-enenitrile (100 g) and propynoic acid methyl ester in DMF (200 ml) was stirred at 25° C. for 2 h and refluxed for additional 1 h. Dowtherm (100 ml) was added and the temperature was rised to 230° C. DMF and MeOH were distilled off. The reaction mixture was cooled down, EtOAc (200 ml) was added and the resulting crystals were filtered off and washed with EtOAc and ether affording the title compound (44.8 g, FP>250° C.).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08278302B2 |
| Source dataset | uspto-grants-2012_10 |
| ORD ID | ord-9776bba37b334543bfef5f55a6d48ddd |
| Source note | uspto-grants-2012_10 |