3-Ethoxy-4-methoxybenzonitrile → (3-Ethoxy-4-methoxyphenyl)methanamine

HRID 1934726

Reaction equation

HRID 1934726 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[C:13]#[N:14])[CH3:8].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>O1CCCC1.C(OCC)(=O)C>[CH2:7]([O:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[CH2:13][NH2:14])[CH3:8]

Participants

6

Reactant 3

HCID 39347693-Ethoxy-4-methoxybenzonitrileHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydride

Product 1

HCID 6486613(3-Ethoxy-4-methoxyphenyl)methanamineYield 100.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of lithium aluminum hydride (1.17 g) in anhydrous tetrahydrofuran (15 mL) was added a solution of 3-ethoxy-4-methoxybenzonitrile (2.73 g) in tetrahydrofuran (15 mL). The mixture was stirred for an hour under water cooling and then for an hour at ambient temperature. Potassium sodium (+)-tartrate aqueous solution was added to the mixture under ice-water cooling. The mixture was diluted with ethyl acetate and the insolubles were filtered off. After evaporation of the filtrate, ethyl acetate was added. The solution was dried over magnesium sulfate and evaporated in vacuo to give 3-ethoxy-4-methoxybenzylamine as yellow oil (2.81 g).

Workup

  1. waitfor an hour at ambient temperature
  2. filtrationthe insolubles were filtered off
  3. customAfter evaporation of the filtrate, ethyl acetate
  4. additionwas added
  5. dry with materialThe solution was dried over magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-bd12492f2f9442299de08c06bcf8f529
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Linked notes

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