2-Bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine → 2-[(5-Amino-2,3-dihydro-2,4,6,7-tetramethylbenzofuran-2-yl)methyl]-2H-isoindole-1,3-dione

HRID 565668Notes

Reaction equation

HRID 565668 reaction equation
Br[CH2:2][C:3]1([CH3:16])[CH2:7][C:6]2[C:8]([CH3:15])=[C:9]([NH2:14])[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]=2[O:4]1.[C:17]1(=[O:27])[NH:21][C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.[K]>CN(C)C(=O)C.O>[NH2:14][C:9]1[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]2[O:4][C:3]([CH2:2][N:21]3[C:17](=[O:27])[C:18]4[C:19](=[CH:23][CH:24]=[CH:25][CH:26]=4)[C:20]3=[O:22])([CH3:16])[CH2:7][C:6]=2[C:8]=1[CH3:15]

Participants

5

Reactant 2

HCID 108505902-Bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamineHCID 24194345Phthalimide potassium salt

Product 1

HCID 221110132-[(5-Amino-2,3-dihydro-2,4,6,7-tetramethylbenzofuran-2-yl)methyl]-2H-isoindole-1,3-dioneYield 56.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

A suspension of 2-bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine (2.0 g) and potassium phthalimide (2.2 g) in N,N-dimethylacetamide (20 mL) was refluxed under nitrogen gas for 3 hours. This reaction mixture was diluted with water and extracted with 2 portions of ethyl acetate. The pooled organic layer was washed with water and saturated aqueous NaCl, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was crystallized from ethyl acetate/diisopropyl ether to provide 1.4 g of the title compound. Yield 56%.

Workup

  1. temperaturewas refluxed under nitrogen gas for 3 hours
  2. extractionextracted with 2 portions of ethyl acetate
  3. washThe pooled organic layer was washed with water and saturated aqueous NaCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-907fbaa4b6c14158945b3e77b1864ad1
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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