Ammonium Hydroxide → HCID 68748372, compound

HRID 333332Notes

Reaction equation

HRID 333332 reaction equation
[C:1]([CH:3]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[CH:14][CH:13]=1)[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])#[N:2].[OH-].[NH4+]>O1CCOCC1.[Ni].[Pd]>[NH2:2][CH2:1][CH:3]([CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[CH:16][CH:17]=1)[C:4]([O:6][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:5]

Participants

6

Reactant 2

HCID 14923Ammonium HydroxideHCID 68746979HCID 68746979, compound

Product 1

HCID 68748372HCID 68748372, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A suspension of tert-butyl 2-cyano-3-(4-(pyridin-2-yl)phenyl)propanoate (150 mg, 0.486 mmol), Raney 2800 nickel (slurry in water) (0.486 mmol), Pd/C (51.8 mg, 0.049 mmol) and ammonium hydroxide (1.894 ml, 48.6 mmol) in dioxane (10 ml) was stirred at room temperature under H2 for 3 hours. The reaction mixture was filtered, and the filtrate was extracted with EtOAc. The combined organic layer was washed with brine and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the title compound. LCMS (condition B): 313.3 (M+1); retention time=0.54 min.

Workup

  1. filtrationThe reaction mixture was filtered
  2. extractionthe filtrate was extracted with EtOAc
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b30637ec6890432fb168b8431ef254c5
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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