Allyl bromide → N-allyl-3-methoxyaniline

HRID 2193084Notes

Reaction equation

HRID 2193084 reaction equation
O1C[CH2:4][CH2:3][CH2:2]1.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[CH:9]=1.C(N(CC)CC)C.C(Br)C=C>C(OCC)(=O)C.O>[CH2:4]([NH:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([O:7][CH3:6])[CH:9]=1)[CH:3]=[CH2:2]

Participants

7

Reactant 4

HCID 7841Allyl bromideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 108243-Methoxyaniline

Product 1

HCID 14069075N-allyl-3-methoxyaniline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 10 mL of a tetrahydrofuran solution containing 1.0 g of m-anisidine, 1.2 mL of triethylamine and 0.70 mL of allyl bromide were added under cooling with ice. The reaction mixture was stirred for 30 minutes. Water and ethyl acetate were added thereto. The organic layer was separated, and the aqueous layer was separated with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1] to obtain 0.36 g of a yellow oily substance, N-allyl-3-methoxyaniline.

Workup

  1. additionwere added
  2. temperatureunder cooling with ice
  3. customThe organic layer was separated
  4. customthe aqueous layer was separated with ethyl acetate
  5. washthe resultant solution was washed with an aqueous saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1]

Sources & evidence

ORD record
ord-88ab9cf3c1ad4450bcd6c585ad4f5386
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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