4-(1-Ethoxyethoxy)-3-methoxybenzonitrile → 1-[4-(1-Ethoxyethoxy)-3-methoxyphenyl]methanamine

HRID 325939Notes

Reaction equation

HRID 325939 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH:12]([O:14][CH2:15][CH3:16])[CH3:13])[C:6]#[N:7].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][NH2:7])[CH:8]=[CH:9][C:10]=1[O:11][CH:12]([O:14][CH2:15][CH3:16])[CH3:13]

Participants

4

Reactant 2

HCID 132924914-(1-Ethoxyethoxy)-3-methoxybenzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 132924921-[4-(1-Ethoxyethoxy)-3-methoxyphenyl]methanamineYield 71.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 5.0 g of 3-methoxy-4-(2-ethoxy-1-oxapropyl)benzonitrile in 25 ml anhydrous THF was added dropwise to 119.5 ml 1 M lithium aluminum hydride in THF. The mixture was refluxed for four hours, cooled to 0° C., and the excess reagent was quenched with 5 N NaOH. The precipitated aluminum salts were removed by filtration and the THF evaporated. The residue was partitioned between 200 ml ether and 75 ml H2O. The remaining ether layer was washed with 75 ml of brine, dried (K2CO3), filtered, and evaporated to yield 3.63 g of 2-methoxy-4-aminomethyl-(2-ethoxy-1-oxapropyl)benzene.

Workup

  1. temperatureThe mixture was refluxed for four hours
  2. customthe excess reagent was quenched with 5 N NaOH
  3. customThe precipitated aluminum salts were removed by filtration
  4. customthe THF evaporated
  5. customThe residue was partitioned between 200 ml ether and 75 ml H2O
  6. washThe remaining ether layer was washed with 75 ml of brine
  7. dry with materialdried (K2CO3)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-b008e4ba6e6740538616b450a392d1f5
Source dataset
uspto-grants-1984_04
Patent number
US04443473

Reaction notes

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