Acetic Acid → HCID 89922622, compound

HRID 921929Notes

Reaction equation

HRID 921929 reaction equation
[NH2:1][C:2]1[C:3]([Cl:16])=[CH:4][C:5](/[C:10](=[CH:12]/[C:13](=[O:15])[CH3:14])/[CH3:11])=[C:6]([CH:9]=1)[C:7]#[N:8].C(O)(=O)C>CO.[OH-].[OH-].[Pd+2]>[NH2:1][C:2]1[C:3]([Cl:16])=[CH:4][C:5]([CH:10]([CH2:12][C:13](=[O:15])[CH3:14])[CH3:11])=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 89923050HCID 89923050, compound

Product 1

HCID 89922622HCID 89922622, compoundYield 60.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

(E)-5-amino-4-chloro-2-(4-oxopent-2-en-2-yl)benzonitrile (120 mg, 0.51 mmol) and Pd(OH)2 on carbon (10% w/w, 10 mg) was suspended in MeOH (3 mL). Acetic acid (0.06 mL) was then added and the reaction was stirred at room temperature under a balloon of H2 for 48 h. The reaction was then filtered through a pad of Celite, washing with EtOAc. The eluent was then concentrated in vacuo and the material was purified on ISCO (0-80% EtOAc/Hexane) to give 5-amino-4-chloro-2-(4-oxopentan-2-yl)benzonitrile (73 mg) as a white solid.

Workup

  1. filtrationThe reaction was then filtered through a pad of Celite
  2. washwashing with EtOAc
  3. concentrationThe eluent was then concentrated in vacuo
  4. customthe material was purified on ISCO (0-80% EtOAc/Hexane)

Sources & evidence

ORD record
ord-b7d082b0359b4b798247009338d3b399
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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