4-Bromo-1-naphthylamine → 4-Amino-1-naphthalenecarbonitrile

HRID 1470501Notes

Reaction equation

HRID 1470501 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](Br)=[CH:4][CH:3]=1.[C:13]([Cu])#[N:14]>CN(C=O)C.[Cu]I>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:13]#[N:14])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 753034-Bromo-1-naphthylamineHCID 178418546HCID 178418546, compound

Product 1

HCID 428284-Amino-1-naphthalenecarbonitrile

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 1-amino-4-bromonaphthalene (5 g, 22.5 mmol) in DMF (30 mL) was added CuCN (10.1 g, 112.5 mmol), CuI (8.7 g, 45 mmol) and the mixture was heated to 120° C. in a sealed tube for 24 h. After completion of the reaction (TLC), the mixture was filtered and the filtrate was evaporated to give the crude product which was purified by column chromatography over silica gel (EtOAc in Hexanes, 5%) to furnish the desired compound.

Workup

  1. customAfter completion of the reaction (TLC)
  2. filtrationthe mixture was filtered
  3. customthe filtrate was evaporated
  4. customto give the crude product which
  5. customwas purified by column chromatography over silica gel (EtOAc in Hexanes, 5%)

Sources & evidence

ORD record
ord-76f163d8a748423c908ef68faff16e23
Source dataset
uspto-grants-2015_04
Patent number
US09006442B2

Reaction notes

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