HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → Methyl 4-cyano-3-nitrobenzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Methyl 3-nitro-4-[[(trifluoromethyl)sulfonyl]oxy]benzoate | HCID 10925511 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Product | Methyl 4-cyano-3-nitrobenzoate | HCID 53419688 | 60.7% |
Reaction Conditions
| Temperature | 100 °C |
|---|
Reaction Steps
3-Nitro-4-trifluoromethanesulfonyloxy-benzoic acid methyl ester (89.7 g, 272 mmol), zinc cyanide (19.2 g, 163 mmol) and tetrakis(triphenylphosphine)palladium(0) (15 g) were suspended in N,N-dimethylformamide (2500 ml). The reaction mixture was stirred for 3 hours at 100° C. under an inert atmosphere. The solvent was evaporated and the residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 3:1) to give 4-cyano-3-nitro-benzoic acid methyl ester (34.0 g, 60.7% yield). 1H-NMR (400 MHz, CDCl3): 8.92 (s, 1H), 8.48 (d, 1H), 8.04 (d, 1H), 4.03 (s, 3H) ppm.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08389766B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-4cca7ba35e2140b094d770e83f2d9273 |
| Source note | uspto-grants-2013_03 |