2-Iodoaniline → 2-(Hex-1-yn-1-yl)aniline

HRID 1602940Notes

Reaction equation

HRID 1602940 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH3:6].I[C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10]>C(N(CC)CC)C.[Cu](I)I.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10])#[C:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 2

HCID 119952-IodoanilineHCID 127321-Hexyne

Product 1

HCID 107973102-(Hex-1-yn-1-yl)aniline

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Procedure

32 mg of copper iodide and 140 mg of bis(triphenylphosphine) palladium chloride, then 2.3 ml of 1-hexyne were added to a solution of 4.4 g of 2-iodoaniline in 100 ml of triethylamine and the mixture was stirred for 15 hours at ambient temperature. After evaporation to dryness, the residue was taken up in ether and the insoluble part was filtered out and washed with ether. The filtrate was evaporated to dryness and the residue was chromatographed on silica (eluant: hexane-ethyl acetate (9-1)) to obtain 3.27 g of the desired product.

Workup

  1. customAfter evaporation to dryness
  2. filtrationthe insoluble part was filtered out
  3. washwashed with ether
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was chromatographed on silica (eluant: hexane-ethyl acetate (9-1))

Sources & evidence

ORD record
ord-5d92b460abfa4dcf9adac400e341dac0
Source dataset
uspto-grants-1999_11
Patent number
US05985894

Reaction notes

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