Methylamine → N-methyl-1-benzofuran-6-amine

HRID 594798Notes

Reaction equation

HRID 594798 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]2[CH:6]=[CH:7][O:8][C:4]=2[CH:3]=1.[CH3:11][NH2:12].CC([O-])=O.[K+]>CN(C=O)C.[OH-].[NH4+].[Cu]I>[CH3:11][NH:12][C:2]1[CH:10]=[CH:9][C:5]2[CH:6]=[CH:7][O:8][C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 6329MethylamineHCID 517044Potassium AcetateHCID 151587226-Bromo-1-benzofuran

Product 1

HCID 118597876N-methyl-1-benzofuran-6-amineYield 33.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-bromo-1-benzofuran (1.0 g, 5.1 mmol), methylamine (2N, 25 mL, 50 mmol), CuI (1.16 g, 6.1 mmol) and KOAc (1.25 g, 12.7 mmol) in DMF (10 mL) was stirred overnight at 100° C. under nitrogen in a sealed tube. The mixture was cooled to r.t., diluted with aqueous ammonium hydroxide, and extracted with EtOAc. The organic layer was concentrated, and the residue was purified by silica gel chromatography to give 250 mg (33%) of the title compound as a yellow oil. [M+H] Calc'd for C9H9NO, 148. Found, 148.

Workup

  1. temperatureThe mixture was cooled to r.t.
  2. extractionextracted with EtOAc
  3. concentrationThe organic layer was concentrated
  4. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-e84a1df9e0b34385b22b7e0e418b700d
Source dataset
uspto-grants-2016_01
Patent number
US09242968B2

Reaction notes

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