2,4-Dichloro-1-(1-methoxy-2-nitro-propyl)-benzene → 1-(2,4-Dichlorophenyl)-1-methoxypropan-2-amine

HRID 1873863Notes

Reaction equation

HRID 1873863 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([O:15][CH3:16])[CH:10]([N+:12]([O-])=O)[CH3:11]>C1COCC1.[Ni].CCO>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([O:15][CH3:16])[CH:10]([NH2:12])[CH3:11]

Participants

4

Reactant 1

HCID 584436852,4-Dichloro-1-(1-methoxy-2-nitro-propyl)-benzene

Product 1

HCID 594032951-(2,4-Dichlorophenyl)-1-methoxypropan-2-amineYield 100%

Reagents, catalysts & solvents 2

HCID 86745698ethanol Raney-nickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2,4-dichloro-1-(1-methoxy-2-nitro-propyl)-benzene (132.2 g, 0.500 mol), was dissolved in THF (3.6 l). The solution was deaerated, RaNi-EtOH (133 g) catalyst was added, and the mixture was hydrogenated at 50 bar at ambient temperature for 23 hours. The catalyst was removed by filtration and the solvent was removed under reduced pressure. 117.1 g (100% of theory) of 2-(2,4-dichlorophenyl)-2-methoxy-1-methyl-ethylamine (compound Z1.14) was obtained in the form of a colourless oil as a mixture of diastereomeres.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b17ba39f1a224e61907c0bb15c8992e0
Source dataset
uspto-grants-2012_11
Patent number
US08304444B2

Reaction notes

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