Sodium Carbonate → 1-(3,4-Dimethoxyphenyl)ethan-1-amine

HRID 2301934Notes

Reaction equation

HRID 2301934 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=[N:13]O)[CH3:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([NH2:13])[CH3:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 2779100Ethanone,1-(3,4-dimethoxyphenyl)-, oxime

Product 1

HCID 31592431-(3,4-Dimethoxyphenyl)ethan-1-amineYield 213.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

3′,4′-Dimethoxyacetophenone oxime (1 gram, 5.1 mmol) was dissolved in 10 milliliters of glacial acetic acid, the solution was flushed with N2 and the palladium on carbon (0.2 grams, 5%) was added. The mixture was treated with 60 psi of H2 in a Parr Type Shaker for 24 hours. The catalyst was filtered off and the filtrate was concentrated to afford a yellow oil which was taken up in water, basified to pH 12 with a saturated solution of sodium carbonate and extracted with methylene chloride. The combined extracts were dried over magnesium sulfate and concentrated to afford 1.97 grams (82%) of product as a yellow oil: 1H NMR (CDCl3) δ7.02-6.75 (m, 3H), 4.08 (q, J1=6.6 Hz, J2=13.1 Hz, 1 H), 3.89 (s, 3H), 3.87 (s, 3H), 1.37 (d , J=6.6 Hz, 3H).

Workup

  1. customthe solution was flushed with N2
  2. additionthe palladium on carbon (0.2 grams, 5%) was added
  3. additionThe mixture was treated with 60 psi of H2 in a Parr Type Shaker for 24 hours
  4. filtrationThe catalyst was filtered off
  5. concentrationthe filtrate was concentrated
  6. customto afford a yellow oil which
  7. extractionextracted with methylene chloride
  8. dry with materialThe combined extracts were dried over magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b50a9f44f01b43d6afca1b5ee3fdbf17
Source dataset
uspto-grants-2002_08
Patent number
US06429221B1

Reaction notes

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