2-Iodoaniline → HCID 66658583, compound

HRID 420814Notes

Reaction equation

HRID 420814 reaction equation
I[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:9][CH:10]([CH3:13])[C:11]#[CH:12]>CCN(CC)CC.CCOCC.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:9][CH:10]([CH3:13])[C:11]#[C:12][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4]

Participants

7

Reactant 2

HCID 119952-IodoanilineHCID 690193-Methylbut-1-yne

Product 1

HCID 66658583HCID 66658583, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 3283Diethyl EtherSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 2-iodoaniline (Aldrich, 5.0 g, 22.8 mmol) in Et3N (50 ml) in a re-sealable pressure tube was added copper (I) iodide (22 mg, 0.114 mmol), Pd(PPh3)2Cl2 (80 mg, 0.114 mmol), and 3-methylbut-1-yne (Alfa Aesar, 3.1 g, 45.7 mmol). The mixture was stirred at room temperature for 20 h and was diluted with Et2O, filtered through Celite, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with 30% Et2O-hexanes to yield 2-(3-methylbut-1-ynyl)aniline (Compound 37) as orange oil.

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash chromatography on silica gel eluting with 30% Et2O-hexanes

Sources & evidence

ORD record
ord-94661b7cf3824e0a9ae5d4b6dd83905a
Source dataset
uspto-grants-2012_01
Patent number
US08097644B2

Reaction notes

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