HCID 58495680, compound → HCID 58495447, compound

HRID 1191064Notes

Reaction equation

HRID 1191064 reaction equation
[CH3:1][C:2]([CH3:16])([CH3:15])[C:3](=[O:14])[CH2:4][O:5][C:6]1[N:11]=[CH:10][C:9]([C:12]#[N:13])=[CH:8][CH:7]=1>CO.Cl.[Pd]>[NH2:13][CH2:12][C:9]1[CH:10]=[N:11][C:6]([O:5][CH2:4][C:3](=[O:14])[C:2]([CH3:15])([CH3:1])[CH3:16])=[CH:7][CH:8]=1

Participants

5

Reactant 1

HCID 58495680HCID 58495680, compound

Product 1

HCID 58495447HCID 58495447, compoundYield 55.7%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Bubble nitrogen into a solution of 6-(3,3-dimethyl-2-oxo-butoxy)-pyridine-3-carbonitrile (400 mg, 1.8 mmol) in methanol (36 mL) with 3 drops of concentrated HCl for 10 min. Add 10% Pd/C (Degussa type E101, 80 mg) and submit the mixture to hydrogenation at atmospheric pressure overnight. Filter the reaction mixture over Celite®. Concentrate the filtrate in vacuo and purify by SCX chromatography to obtain the title compound (223 mg, 55%). MS (ES+) m/z: 223 (M+H)+.

Workup

  1. customat atmospheric pressure overnight
  2. filtrationFilter the reaction mixture over Celite®
  3. concentrationConcentrate the filtrate in vacuo
  4. custompurify by SCX chromatography

Sources & evidence

ORD record
ord-c9a468f984e041839807f58de1167fac
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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