Water → Benzofuran

HRID 1732578Notes

Reaction equation

HRID 1732578 reaction equation
CN(C)C([C:5]1[CH:18]=[CH:17][C:8]2[CH:9]=[C:10](CCCCN)[O:11][C:7]=2[CH:6]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[O:11]1[C:7]2[CH:6]=[CH:5][CH:18]=[CH:17][C:8]=2[CH:9]=[CH:10]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 20303938N,N-dimethyl-2-(4-aminobutyl)benzofuran-6-carboxamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 9223Benzofuran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N,N-dimethyl-2-(4-aminobutyl)benzofuran-6-carboxamide (13.0 g., 0.05 mole) in tetrahydrofuran (60 ml.) is added dropwise with stirring to lithium aluminum hydride (3.0 g., 0.08 mole) in tetrahydrofuran (60 ml.) at 25°-30° C. The mixture is stirred for 2 hours at 25°-30° C. and then is treated successively with 3 g. of water, 3 g. of 15% sodium hydroxide solution and 9 g. of water. The solid precipitate is removed by filtration. The tetrahydrofuran solution is evaporated at reduced pressure to provide 2-(4-aminobutyl)-6-dimethylaminomethyl)benzofuran.

Workup

  1. additionis treated successively with 3 g
  2. customThe solid precipitate is removed by filtration
  3. customThe tetrahydrofuran solution is evaporated at reduced pressure

Sources & evidence

ORD record
ord-571fabba0df1450b81845ecf6193e1cf
Source dataset
uspto-grants-1980_12
Patent number
US04238487

Reaction notes

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