Ethanol → C-(6-Phenoxy-benzofuran-2-yl)-methylamine

HRID 1171211Notes

Reaction equation

HRID 1171211 reaction equation
C(O)C.[O:4]([C:11]1[CH:31]=[CH:30][C:14]2[CH:15]=[C:16]([CH2:18][N:19]3C(=O)C4C(=CC=CC=4)C3=O)[O:17][C:13]=2[CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O.NN>O>[O:4]([C:11]1[CH:31]=[CH:30][C:14]2[CH:15]=[C:16]([CH2:18][NH2:19])[O:17][C:13]=2[CH:12]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 576082842-(6-Phenoxy-benzofuran-2-ylmethyl)-isoindole-1,3-dione

Product 1

HCID 57608283C-(6-Phenoxy-benzofuran-2-yl)-methylamineYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ethanol (5 mL) solution of 2-(6-phenoxy-benzofuran-2-ylmethyl)-isoindole-1,3-dione (209 mg, 566 μmol) described in Production Example 49-1-3 was added hydrazine hydrate (549 μL, 11.3 mmol) at room temperature, which was stirred for 1 hour while heating under reflux. Water was added to the reaction solution at room temperature followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under a reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:1) to obtain the title compound (92 mg, 68%) as a colorless oil.

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under a reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:1)

Sources & evidence

ORD record
ord-7021c0f8a9bd451380fcc00581f585a4
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

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