HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → Methyl 3-cyano-4-hydroxybenzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Methylamine | HCID 6329 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | Methyl 4-hydroxy-3-iodobenzoate | HCID 11346465 | — |
| Product | Methyl 3-cyano-4-hydroxybenzoate | HCID 11769089 | 144.6% |
Reaction Steps
To a solution of 1 in DMF (158 mg, 0.41 mmol) were added amino acid 2 (100 mg, 0.52 mmol) and DIEA (272 μL, 0.16 mmol). The reaction was stirred for 14 h. Methylamine (2 M in THF, 0.4 mL) and HBTU (295 mg, 0.78 mmol) were then added. The reaction mixture was stirred for 5 h. The product was purified by RP-HPLC using a mixture of acetonitrile and H2O to give 3 (105 mg, 63%). LRMS (M+H+) m/z 401.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07582668B2 |
| Source dataset | uspto-grants-2009_09 |
| ORD ID | ord-03a518be247d44e0bfea6d36bb154761 |
| Source note | uspto-grants-2009_09 |