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

HRID 398992Notes

Reaction equation

HRID 398992 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 and 140 mg of bistriphenyl phosphine palladium chloride and 2.3 ml of 1-hexyne were added to a solution of 4.4 g of 2-iodo aniline in 100 ml of triethylamine and the mixture was stirred for 15 hours at ambient temperature, then evaporated to dryness. The residue was taken up in ether and the insoluble part was filtered out, 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 of the desired product.

Workup

  1. customevaporated to dryness
  2. filtrationthe insoluble part was filtered out
  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-d0b856978e754253ae4b405c86b10e89
Source dataset
uspto-grants-1998_10
Patent number
US05817674

Reaction notes

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