2-Methoxy-β-nitrostyrene → 2-Methoxyphenethylamine

HRID 1843851Notes

Reaction equation

HRID 1843851 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]=[CH:10][N+:11]([O-])=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][NH2:11]

Participants

4

Reactant 2

HCID 979212-Methoxy-β-nitrostyreneHCID 21226445Aluminium lithium hydride

Product 1

HCID 748962-MethoxyphenethylamineYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Using analogous reaction conditions and workup as described in Example 1, step 2, 1-methoxy-2-(2-nitro-vinyl)-benzene (I-13a: 4.5 g, 25.1396 mmol) in dry THF (50 mL) was reacted with LAH (1.91 g, 50.2793 mmol) in dry THF (50 mL) to afford 2.7 g of the crude product which was used in the next step without further purification.

Workup

  1. customreaction conditions and workup

Sources & evidence

ORD record
ord-5fc3c981a2e543f9a03c92b5623af1df
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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