Hydrochloric Acid → HCID 59403298, compound

HRID 1873866Notes

Reaction equation

HRID 1873866 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([NH:15][O:16][CH3:17])[CH:10]([N+:12]([O-])=O)[CH3:11].Cl>[Zn].CC(O)C>[NH2:12][CH:10]([CH3:11])[CH:9]([NH:15][O:16][CH3:17])[C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59403300HCID 59403300, compound

Product 1

HCID 59403298HCID 59403298, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 3776IsopropanolSolvent

Procedure

N-[1-(2,4-dichloro-phenyl)-2-nitro-propyl]-O-methyl-hydroxylamine (0.123 g, 0.44 mmol), was dissolved with i-PrOH (9 ml) and treated with 1N HCl (4.4 ml, 4.4 mmol). Zinc dust (0.58 g, 8.8 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 (15 ml), stirred for 15 minutes and filtered through a small plug of Celite, washing with ethylacetate (40 ml). The organic extract was separated, dried over anhydrous MgSO4 an filtered and the solvent was removed under reduced pressure. 110 mg (100% of theory) of N-[2-Amino-1-(2,4-dichloro-phenyl)-propyl]-O-methyl-hydroxylamine (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 (15 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. customwas separated
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationan filtered
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-844c5b0158204b7fa218af69ab350df5
Source dataset
uspto-grants-2012_11
Patent number
US08304444B2

Reaction notes

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