2-Bromotoluene → N-(2-Methylphenyl)naphthalen-1-amine

HRID 1776079Notes

Reaction equation

HRID 1776079 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.Br[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19].CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:14]1([CH3:19])[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[NH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 72362-BromotolueneHCID 86401-NaphthylamineHCID 23676156Sodium t-butoxide

Product 1

HCID 20511057N-(2-Methylphenyl)naphthalen-1-amineYield 91.5%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  1. customwas degassed
  2. dry with materialdried over Na2SO4
  3. custompurified by flash column
  4. customAfter removal of solvents

Sources & evidence

ORD record
ord-27dcc43437f24cda8780e2f38c43f5b4
Source dataset
uspto-grants-2016_02
Patent number
US09263681B2

Reaction notes

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