Water → 2-Benzo[b]furan-3-ylethylamine

HRID 621499

Reaction equation

HRID 621499 reaction equation
[C:1]([CH2:3][C:4]1[C:5]2[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=2[O:7][CH:8]=1)#[N:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C(OCC)C>[O:7]1[CH:8]=[C:4]([CH2:3][CH2:1][NH2:2])[C:5]2[CH:12]=[CH:11][CH:10]=[CH:9][C:6]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 2769401Benzofuran-3-acetonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 124208122-Benzo[b]furan-3-ylethylamineYield 79.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 3.97 g (0.025 mole) of 3-cyanomethylbenzo[b]furan in 200 mL of diethyl ether was slowly added to a refluxing suspension of 3.84 g (0.1 mole) of lithium aluminum hydride in 400 mL of ether. The reaction was heated 3 hours., cooled and water was slowly added. The suspension was filtered through a pad of filter aid and the filtrate was evaporated to give 3.2 g of oily product. The hydrochloride salt has m.p. 183°-185° C.

Workup

  1. temperatureThe reaction was heated 3 hours
  2. temperature, cooled
  3. filtrationThe suspension was filtered through a pad of filter aid
  4. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-2118182ae9544f038ba02bbca9f31c8c
Source dataset
uspto-grants-1989_04
Patent number
US04824849

Linked notes

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