HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1776079Generated: November 1, 2026
2-Bromotoluene → N-(2-Methylphenyl)naphthalen-1-amine
https://huagongshe.com/reaction/1776079
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2-Bromotoluene | HCID 7236 | — |
| Reactant | 1-Naphthylamine | HCID 8640 | — |
| 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-(2-Methylphenyl)naphthalen-1-amine | HCID 20511057 | 91.5% |
Reaction Steps
A mixture of 1-aminonaphthalene (7.15 g, 50 mmol), 1-bromo-2-methylbenzene (8.5 g, 50 mmol), Pd(dppf)Cl2 (1.0 g, 1.36 mmol), sodium tert-butoxide (9.6 g, 0.1 mol) in toluene (120 mL) was degassed and heated at about 100° C. overnight. The resulting mixture was worked up with ethyl acetate/brine, dried over Na2SO4, loaded on silica gel and purified by flash column using eluents of hexanes to hexanes/dichloromethane 9:1. After removal of solvents, an oil (Compound 20) was obtained, 10.2 g in 91.5% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09263681B2 |
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| Source dataset | uspto-grants-2016_02 |
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| ORD ID | ord-27dcc43437f24cda8780e2f38c43f5b4 |
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| Source note | uspto-grants-2016_02 |
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