1-(4-Carbomethoxyphenyl)propan-2-one oxime → Methyl 4-(2-aminopropyl)benzoate

HRID 1633114Notes

Reaction equation

HRID 1633114 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12](=[N:14]O)[CH3:13])=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2].[H][H]>C(Cl)(Cl)Cl.[Pt]=O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([CH3:13])[NH2:14])=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2]

Participants

5

Reactant 2

HCID 867397271-(4-Carbomethoxyphenyl)propan-2-one oximeHCID 178418361HCID 178418361, compound

Product 1

HCID 15034329Methyl 4-(2-aminopropyl)benzoate

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 6212ChloroformSolvent

Procedure

1-(4-Carbomethoxyphenyl)propan-2-one oxime (10.0 g) in absolute alcohol (200 ml) and chloroform (25 ml) was hydrogenated on a Parr hydrogenator at 50 psi and at 50° in the presence of platinum oxide (250 mg) until hydrogen uptake had ceased. The catalyst was removed and the residue was recrystallised as the hydrochloride from methanol/ethyl acetate, mp 206°-210° (8.5 g). γ(d6DMSO) 8.84 (3H, d, 6 Hz), 6.2-7.5 (3H, m), 6.17 (3H, s), 2.59 (2H, d, J=8 Hz), 2.09 (2H, d, J=8 Hz), 1.50 (2H, br).

Workup

  1. customThe catalyst was removed
  2. customthe residue was recrystallised as the hydrochloride from methanol/ethyl acetate, mp 206°-210° (8.5 g)

Sources & evidence

ORD record
ord-22971fd90c0648a2a8b3bd309cc02df0
Source dataset
uspto-grants-1984_10
Patent number
US04478849

Reaction notes

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