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

HRID 2260821Notes

Reaction equation

HRID 2260821 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>[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

5

Reactant 2

HCID 119952-IodoanilineHCID 127321-Hexyne

Product 1

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

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8471TriethylamineSolvent

Procedure

32 mg of copper iodide, 140 mg of bistriphenyl phosphine palladium chloride and then 2.3 ml of 1-hexyne were added to a solution of 4.4 g of 2-iodo aniline in 100 ml of triethylamine. The mixture was stirred for 15 hours at ambient temperature, followed by evaporating to dryness and taking up in ether. The insoluble part was filtered off, washed with ether and the ethereal fractions were evaporated to dryness. The residue was chromatographed on silica (eluant: hexane--ethyl acetate (9-1)) to obtain 3.27 g of the desired product.

Workup

  1. customby evaporating to dryness
  2. filtrationThe insoluble part was filtered off
  3. washwashed with ether
  4. customthe ethereal fractions were evaporated to dryness
  5. customThe residue was chromatographed on silica (eluant: hexane--ethyl acetate (9-1))

Sources & evidence

ORD record
ord-31b5fe1d32974c9aaca45330bc7563f0
Source dataset
uspto-grants-1995_12
Patent number
US05478938

Reaction notes

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