Sodium Hydroxide → 2-(2,4-Dimethoxyphenyl)ethan-1-amine

HRID 978239

Reaction equation

HRID 978239 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11]=[CH:12][N+:13]([O-])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1.CCOCC>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][CH2:12][NH2:13]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 2754052,4-Dimethoxy-1-(2-nitroethenyl)benzeneHCID 21226445Aluminium lithium hydride

Product 1

HCID 4176042-(2,4-Dimethoxyphenyl)ethan-1-amine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

The ethylene compound in 500 ml of tetrahydrofuran was added to 36.7 g of lithium aluminum hydride in 500 ml of ether. After a reflux period of 1.5 hours, the mixture was combined with 184 ml of 1N sodium hydroxide solution. The resulting cake was separated by filtration and washed with 200 ml of hot tetrahydrofuran. The ethereal extracts and mother liquors were stripped. The residual oil was taken into chloroform, dried and stripped to give 94.9 g of 2,4-dimethoxyphenethylamine as an oil.

Workup

  1. customThe resulting cake was separated by filtration
  2. washwashed with 200 ml of hot tetrahydrofuran
  3. customdried

Sources & evidence

ORD record
ord-a78991df21cf4b29a5d8486951a53951
Source dataset
uspto-grants-1987_05
Patent number
US04663482

Linked notes

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