Hydrochloric Acid → HCID 22063875, compound

HRID 1828176Notes

Reaction equation

HRID 1828176 reaction equation
[CH:1]1([N:6]2[C:10]3[CH:11]=[CH:12][C:13]([C:15](=[O:26])[C:16]([C:19]4[CH:20]=[C:21]([CH3:25])[CH:22]=[CH:23][CH:24]=4)=[N:17]O)=[CH:14][C:9]=3[N:8]([CH3:27])[C:7]2=[O:28])[CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:29].[H][H]>C(O)C.C(OCC)C.[Pd]>[ClH:29].[NH2:17][CH:16]([C:19]1[CH:20]=[C:21]([CH3:25])[CH:22]=[CH:23][CH:24]=1)[CH:15]([C:13]1[CH:12]=[CH:11][C:10]2[N:6]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[C:7](=[O:28])[N:8]([CH3:27])[C:9]=2[CH:14]=1)[OH:26]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 86587986HCID 86587986, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22063875HCID 22063875, compoundYield 92.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

1-(1-Cyclopentyl-3-methyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-yl)-2-m-tolyl-ethane-1,2-dione 2-oxime (5 gm, 13.2 mmol) was dissolved in ethanol (300 mL) in a Parr bottle. Concentrated HCl (3.3 mL, 40 mmol) was added, followed by 10% Pd on carbon (approximately 0.5 gm). The resulting mixture was placed on a Parr hydrogenation apparatus and hydrogenated at a hydrogen pressure of 40 psi. Hydrogen consumption slowed considerably after 3 hours, with the amino ketone being formed initially. Hydrogenation was continued overnight, after which time the reaction was determined to be complete. The mixture was filtered through a celite plug and the filtrate was concentrated in vacuo to afford a viscous yellow oil, which was triturated/repulped in diethyl ether to afford 4.90 gm of a white solid.

Workup

  1. customHydrogen consumption
  2. customformed initially
  3. waitHydrogenation was continued overnight
  4. filtrationThe mixture was filtered through a celite plug
  5. concentrationthe filtrate was concentrated in vacuo
  6. customto afford a viscous yellow oil, which

Sources & evidence

ORD record
ord-0f465ae1d23243bfad305f925e3ba83a
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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