HCID 86732868, compound → HCID 54052269, compound

HRID 1579321Notes

Reaction equation

HRID 1579321 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[C:5]([C:21]#[N:22])=[CH:6][CH:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10](OC)=[C:9]([O:17][CH3:18])[C:8]1=C=O)[CH3:2].[H][H]>[Pd].[Hg].C(O)C>[CH2:1]([O:3][C:4](=[O:23])[C:5]([C:21]#[N:22])=[CH:6][CH:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([C:4]([O:3][CH3:1])=[O:23])=[C:9]([O:17][CH3:18])[CH2:8]1)[CH3:2]

Participants

6

Reactant 2

HCID 86732868HCID 86732868, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54052269HCID 54052269, compound

Reagents, catalysts & solvents 3

HCID 23931MercuryCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 10.6 g. of α-cyano-3,5-dimethoxy-4-methoxy-carbonyl-cinnamic acid ethyl ester in 500 ml. of ethanol was hydrogenated in the presence of 0.5 g. of palladium-on-carbon (5%) at room temperature and 760 mm. of mercury. After the uptake of an equivalent of hydrogen (810 ml.), the hydrogenation was interrupted. The catalyst and partially precipitated product were removed by filtration with suction and washed on the filter with benzene. The filtrate was evaporated to dryness. The residue was recrystallized from ethyl acetate and yielded α-cyano-3,5-dimethoxy-4-methoxycarbonyl-dihydro-cinnamic acid ethyl ester having a m.p. of 119°-121°C.

Workup

  1. customat room temperature
  2. customThe catalyst and partially precipitated product were removed by filtration with suction
  3. washwashed on the
  4. filtrationfilter with benzene
  5. customThe filtrate was evaporated to dryness
  6. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-684e98acca04489b8a9c3d6dba0d0d41
Source dataset
uspto-grants-1976_01
Patent number
US03931181

Reaction notes

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