Acetonitrile → 5-Nitro-2-prop-1-ynyl-phenylamine

HRID 2079912

Reaction equation

HRID 2079912 reaction equation
Br[C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH2:4].C(N([CH2:17][CH3:18])CC)C.[C:19](#N)C>[Cu]I>[N+:9]([C:6]1[CH:7]=[CH:8][C:2]([C:19]#[C:17][CH3:18])=[C:3]([NH2:4])[CH:5]=1)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 826072-Bromo-5-nitroaniline

Product 1

HCID 671007405-Nitro-2-prop-1-ynyl-phenylamine

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

Stir a mixture of 2-bromo-5-nitroaniline 16 (2.81 g, 12.95 mmol), dichlorobis(triphenylphospine) palladium (II) (0.45 g, 0.65 mmol), and copper (I) iodide (0.12 g, 0.65 mmol) in anhydrous acetonitrile (10 mL) under inert atmosphere. Saturate the mixture with propyne gas, then add triethyl amine (3.6 mL, 25.90 mmol), seal the vessel, and stir at ambient temperature 14 hours. Concentrate the mixture in vacuo, suspend in 100 mL diethylether, add celite, and filter. Concentrate the filtrate in vacuo and chromatograph the residue over silica gel, eluting with hexanes/ethyl acetate (9:1 v/v) to afford the title compound, 1.75 g (76%). LRMS (API ES+)=177.0 (M+H).

Workup

  1. concentrationSaturate the mixture with propyne gas
  2. stirringstir at ambient temperature 14 hours
  3. concentrationConcentrate the mixture in vacuo
  4. additionadd celite
  5. filtrationfilter
  6. concentrationConcentrate the filtrate in vacuo and chromatograph the residue over silica gel
  7. washeluting with hexanes/ethyl acetate (9:1 v/v)

Sources & evidence

ORD record
ord-1ff459fe65ad4018aea050ce3b4c0d14
Source dataset
uspto-grants-2011_04
Patent number
US07932284B2

Linked notes

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