3-Methoxy--nitrostyrene → 3-Methoxyphenethylamine

HRID 1843843Notes

Reaction equation

HRID 1843843 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH:9]=[CH:10][N+:11]([O-])=O)[CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH2:11])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 2614113-Methoxy--nitrostyreneHCID 21226445Aluminium lithium hydride

Product 1

HCID 748663-MethoxyphenethylamineYield 73.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using analogous reaction conditions and workup as described in Example 1, step 2, 1-methoxy-3-(2-nitro-vinyl)-benzene (I-11a: 10.5 g, 58.659 mmol) in dry THF (110 mL) was reacted with LAH (6.68 g, 175.97 mmol) to afford 6.5 g of the product (73% yield).

Workup

  1. customreaction conditions and workup

Sources & evidence

ORD record
ord-35b41d3331604e3388d0978fdce67f35
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

Loading…