Ethyl 3-(3,4-dimethoxyanilino)but-2-enoate → Ethyl 3-(3,4-dimethoxyanilino)butanoate

HRID 597192Notes

Reaction equation

HRID 597192 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[NH:6][C:7]([CH3:14])=[CH:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]>C(O)(=O)C.C(Cl)(Cl)Cl.[Pt]=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[NH:6][CH:7]([CH3:14])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 1

HCID 70638975Ethyl 3-(3,4-dimethoxyanilino)but-2-enoate

Product 1

HCID 21439734Ethyl 3-(3,4-dimethoxyanilino)butanoateYield 99.2%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 30.0 g of the product of Example 1 (m.p. 59°-60°), and 2.0 g of platinum oxide in 250 ml of acetic acid was hydrogenated in a Paar shaker at 50 p.s.i.; reduction was complete in 1 hr. The mixture was filtered and concentrated under reduced pressure, to give an amber oil which was dissolved in chloroform and washed with sodium bicarbonate solution followed by saturated sodium chloride. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to give 30.0 g of an amber oil which was used in the next step without further purification. A sample of oil was converted to the hydrochloride salt, m.p. 137.5°-139°. An equivalent sample of the hydrochloride salt (m.p. 138°-139.5°) was analyzed.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customto give an amber oil which
  4. washwashed with sodium bicarbonate solution
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c38154bd80bf48879b2262a20f99b05a
Source dataset
uspto-grants-1977_03
Patent number
US04013662

Reaction notes

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