Hydrochloric Acid → HCID 58841411, compound

HRID 32110Notes

Reaction equation

HRID 32110 reaction equation
[CH3:1][N:2]([CH3:18])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[N:16]O)[CH2:11][CH2:10][CH2:9]2.Cl>[Pd].CCO>[CH3:1][N:2]([CH3:18])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]([NH2:16])[CH2:11][CH2:10][CH2:9]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 724406286-(2-dimethylamino-ethoxy)-3,4-dihydro-2H-naphthalen-1-one Oxime

Product 1

HCID 58841411HCID 58841411, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 6-(2-dimethylamino-ethoxy)-3,4-dihydro-2H-naphthalen-1-one oxime (0.3 g, 1.2 mmol), EtOH (12 mL), Pd/C (Aldrich, 0.13g, 0.12 mmol), and concentrated HCl (0.24 mL) was purged with H2 and connected to a H2 balloon overnight at RT. The catalyst was filtered through Celite® and washed with MeOH. The filtrate was concentrated in vacuo. The residue was added saturated NaHCO3 and extracted with CH2Cl2. The organic solution was dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by silica gel chromatography (5%-10% MeOH—CH2Cl2) to afford the compound as a colorless oil. MS (ESI): 235 (M+H)+.

Workup

  1. customwas purged with H2
  2. customconnected to a H2 balloon overnight at RT
  3. filtrationThe catalyst was filtered through Celite®
  4. washwashed with MeOH
  5. concentrationThe filtrate was concentrated in vacuo
  6. additionThe residue was added saturated NaHCO3
  7. extractionextracted with CH2Cl2
  8. dry with materialThe organic solution was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude product was purified by silica gel chromatography (5%-10% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-6da1dde5e22f4bc7ada87f20850fec67
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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