Hydrochloric Acid → Hydrochloric Acid

HRID 2414413Notes

Reaction equation

HRID 2414413 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[C:17]([C:19]#[N:20])[CH:16]=[CH:15][C:14]=1[CH:21]=[CH:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=O)(C)(C)C.[H][H].[ClH:30]>C(OCC)(=O)C.O1CCOCC1.[Pd]>[ClH:30].[NH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[C:17]([C:19]#[N:20])[CH:16]=[CH:15][C:14]=1[CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 69922571HCID 69922571, compoundHCID 178418361HCID 178418361, compound

Product 2

HCID 313Hydrochloric AcidHCID 22645187HCID 22645187, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

3.8 g (10.2 mmol) of ethyl 3-[2-(3-(t-butoxycarbonylamino)propoxy)-4-cyanophenyl]acrylate was dissolved in 100 ml of ethyl acetate. 700 mg of 10% palladium/carbon (50% hydrous) was added to the obtained solution, and they were stirred in the presence of hydrogen for 3 hours. The reaction solution was filtered through Celite. The solvent was evaporated, and the obtained crude product was dissolved in 50 ml of 4 N solution of hydrogen chloride in dioxane. The obtained solution was stirred overnight. The solvent was evaporated to obtain hydrochloride of the crude title compound.

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. customThe solvent was evaporated
  3. customthe obtained crude product
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-f9525e6de7be4250a890fbcff8163d25
Source dataset
uspto-grants-2004_11
Patent number
US06812231B2

Reaction notes

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