Hydrochloric Acid → 1-Amino-3-(3,4-dimethoxyphenyl)-3-methylbutan-2-one hydrochloride

HRID 1627333Notes

Reaction equation

HRID 1627333 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH3:19])([CH3:18])[C:12](=[O:17])[CH2:13][N+:14]([O-])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H][H].[ClH:22]>C(O)(=O)C.[Pd]>[ClH:22].[NH2:14][CH2:13][C:12](=[O:17])[C:11]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 866622423-(3,4-Dimethoxyphenyl)-3-methyl-1-nitrobutan-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 667406301-Amino-3-(3,4-dimethoxyphenyl)-3-methylbutan-2-one hydrochlorideYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 3-(3,4-dimethoxyphenyl)-3-methyl-1-nitrobutan-2-one (400 mg, 1.50 mmol) in acetic acid (6 mL) and conc HCl (2 mL) was added 10% Pd/C (400 mg) in a pressure vessel. The mixture was hydrogenated under 60 psi hydrogen for 48 h and then filtered. The residue was concentrated and triturated with Et2O to give 1-amino-3-(3,4-dimethoxyphenyl)-3-methylbutan-2-one hydrochloride (306 mg, 75%). 1H NMR (400 MHz, DMSO-d6) δ 8.22 (brs, 2H), 6.90 (d, 1H), 6.80 (dd, 1H), 6.72 (d, 1H), 3.73 (s, 3H), 3.70 (s, 3H), 3.68 (s, 2H), 1.42 (s, 6H).

Workup

  1. filtrationfiltered
  2. concentrationThe residue was concentrated
  3. customtriturated with Et2O

Sources & evidence

ORD record
ord-de86ad2cce524c89ac983332f234b193
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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