Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2-Naphthylamine | HCID 7057 | — |
| Reactant | Iodobenzene | HCID 11575 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | N-phenyl-2-naphthylamine | HCID 8679 | 43% |
Reaction Steps
A mixture of 2-naphthylamine (8.0 g, 55.9 mmol), iodobenzene (12.24 g, 60 mmol), Pd(dppf)Cl2 (0.731 g, 1 mmol) and sodium tert-butoxide (NaOBut) (5.76 g, 60 mmol) in toluene (200 mL) was degassed and heated at 120° C. overnight. The whole was poured into ethyl acetate (250 mL), washed with brine, dried over Na2SO4, loaded on silica gel and purified by flash column (hexanes to hexanes/dichloromethane 10:1). The desired fraction was collected, and concentrated. A white solid precipitated, which was filtered to give the product (Compound 20) (5.30 g, in 43% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09172051B2 |
|---|
| Source dataset | uspto-grants-2015_10 |
|---|
| ORD ID | ord-3f6f17bc18ad4ac08a4cd3ebc8318a5d |
|---|
| Source note | uspto-grants-2015_10 |
|---|
