HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 2-methyl-4-(1H-pyrazol-1-yl)aniline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Pyrazole | HCID 1048 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | trans-N,N'-dimethyl-1,2-cyclohexanediamine | HCID 2733821 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | 2-methyl-4-(1H-pyrazol-1-yl)aniline | HCID 14450261 | 70.3% |
Reaction Steps
A solution of intermediate 82 (200 mg, 0.7 mmol), 1H-pyrazole (95 mg, 2 eq), CuI (133 mg, 1 eq), K2CO3 (290 mg, 2.1 eq) and (1R,2R)-diaminomethylcyclohexane (100 mg, 1 eq) in anh. NMP (1 mL), under N2, was heated at 150° C. for 6 hr. It was cooled down to r.t. and poured into water. EtOAc was added and the phases were separated. The aqueous layer was further extracted with EtOAc (2×10 mL). The combined organic extracts were dried over anh. Na2SO4, the solids were filtered and the solvent evaporated. The residue was purified by flash-chromatography (silica gel, cHex/EtOAc 8:2) to give the title compound as a white solid (85.6 mg, 70%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07427630B2 |
| Source dataset | uspto-grants-2008_09 |
| ORD ID | ord-2f001b2f271244129c6d25a97321b00c |
| Source note | uspto-grants-2008_09 |