Hydrochloric Acid → HCID 22041748, compound

HRID 1790299Notes

Reaction equation

HRID 1790299 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[C:15](=[O:20])[C:16](=[N:18]O)[CH3:17].O.[ClH:22]>C(O)C.[Pd]>[ClH:22].[NH2:18][CH:16]([CH3:17])[C:15]([C:4]1[CH:5]=[C:6]([O:13][CH3:14])[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[O:2][CH3:1])=[O:20]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 865927571-(1,4-Dimethoxynaphthalen-2-yl)-propane-1,2-dione 2-oxime

Product 1

HCID 22041748HCID 22041748, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-(1,4-dimethoxynaphthalen-2-yl)-propane-1,2-dione 2-oxime (1 g, 3.66 mmol, Example 2, Step B) in 1 M hydrogen chloride in ethanol (50 mL) was added Pd/C 10% (100 mg), The mixture was hydrogenated on a Parr hydrogenator apparatus under 40–50 psi pressure for 12 h. The catalyst was separated by filtration and the solvent removed in vacuo to give a white solid: 1H NMR (DMSO-d) δ 1.14 (d, 3H, CH3), 3.96 (s, 3H, OH3), 4.01 (s, 3H, OCH3), 5.03 (m, 1H, CH), 7.08 (s, 1H, Ar—H), 7.73 (m, 2H, Ar—H), 8.19 (m, 2H, Ar), 8.50 (bs, 3H, NH3+); Analysis calcd. for C15H17NO3.HCl.0.2 H2O: C, 53.62; H, 5.88; N, 4.81. Found: C, 53.53; H, 5.56; N, 4.77.

Workup

  1. customThe catalyst was separated by filtration
  2. customthe solvent removed in vacuo
  3. customto give a white solid

Sources & evidence

ORD record
ord-c8e7cb25be944baf86677b3c5e4b9408
Source dataset
uspto-grants-2006_07
Patent number
US07071225B2

Reaction notes

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