2-Naphthylamine → N-phenyl-2-naphthylamine

HRID 1755519Notes

Reaction equation

HRID 1755519 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[NH2:11].I[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.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:13]1([NH:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 70572-NaphthylamineHCID 11575IodobenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 8679N-phenyl-2-naphthylamineYield 43%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
120 °C

Procedure

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).

Workup

  1. customwas degassed
  2. additionThe whole was poured into ethyl acetate (250 mL)
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. custompurified by flash column (hexanes to hexanes/dichloromethane 10:1)
  6. customThe desired fraction was collected
  7. concentrationconcentrated
  8. customA white solid precipitated
  9. filtrationwhich was filtered

Sources & evidence

ORD record
ord-3f6f17bc18ad4ac08a4cd3ebc8318a5d
Source dataset
uspto-grants-2015_10
Patent number
US09172051B2

Reaction notes

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