Hydrochloric Acid → HCID 2959448, compound

HRID 2045799Notes

Reaction equation

HRID 2045799 reaction equation
[C:1]([CH:3]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])#[N:2].[ClH:16]>C(O)C.[Pd]>[ClH:16].[NH2:2][CH2:1][CH:3]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 12414061Ethyl 3-cyano-3-phenylpropanoate

Product 1

HCID 2959448HCID 2959448, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl 3-cyano-3-phenylpropanoate 2 (9.27 g, 45.6 mmol) in ethanol (70 mL) was added concentrated hydrochloric acid (2.4 mL) followed by 10% palladium on carbon (1.0 g) and the reaction hydrogenated at 80 psi for 18 h. The mixture was filtered through celite and concentrated in vacuo. The residue was triturated in ether and filtered to give 2 (4.97 g in 2 crops, 45%) as a white solid.

Workup

  1. customthe reaction hydrogenated at 80 psi for 18 h
  2. filtrationThe mixture was filtered through celite and
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated in ether
  5. filtrationfiltered
  6. customto give 2 (4.97 g in 2 crops, 45%) as a white solid

Sources & evidence

ORD record
ord-a1262f8e117d4da398c21aec6611a8b4
Source dataset
uspto-grants-2013_11
Patent number
US08592395B2

Reaction notes

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