Hydrochloric Acid → 1-(2,4-Dichlorophenyl)-1-methoxypropan-2-amine

HRID 1873862Notes

Reaction equation

HRID 1873862 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].Cl>[Zn].CC(O)C>[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

5

Reactant 2

HCID 313Hydrochloric AcidHCID 584436852,4-Dichloro-1-(1-methoxy-2-nitro-propyl)-benzene

Product 1

HCID 594032951-(2,4-Dichlorophenyl)-1-methoxypropan-2-amineYield 77.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 3776IsopropanolSolvent

Procedure

2,4-dichloro-1-(1-methoxy-2-nitro-propyl)-benzene (0.35 g, 1.32 mmol), was dissolved with i-PrOH (27 ml) and treated with 1N HCl (13.2 ml, 13.2 mmol). Zinc dust (1.73 g, 26.4 mmol) was then added in small portions over 15 minutes and the solution allowed to stir for two hours at ambient temperature. The suspension was quenched by addition of saturated NaHCO3 (45 ml), stirred for 15 minutes and filtered through a small plug of Celite, washing with ethylacetate (40 ml). The organic extract was dried over anhydrous MgSO4, filtered and the solvent was removed under reduced pressure. 240 mg (77.6% 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 suspension was quenched by addition of saturated NaHCO3 (45 ml)
  2. stirringstirred for 15 minutes
  3. filtrationfiltered through a small plug of Celite
  4. washwashing with ethylacetate (40 ml)
  5. extractionThe organic extract
  6. dry with materialwas dried over anhydrous MgSO4
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d33e75b0bc3b4eb08f2eee1a1703869b
Source dataset
uspto-grants-2012_11
Patent number
US08304444B2

Reaction notes

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