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

HRID 612438Notes

Reaction equation

HRID 612438 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 choride and 2.3 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, wash 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. customevaporated to dryness
  2. filtrationthe insoluble part was filtered out
  3. washwash 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-7dbfd8fe317d4580a65e0117eabea4e4
Source dataset
uspto-grants-1999_12
Patent number
US06004979

Reaction notes

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