Hydrochloric Acid → HCID 22625614, compound

HRID 277660Notes

Reaction equation

HRID 277660 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]2[CH:17]=1.Cl.[H][H]>[Pt]=O.C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[CH2:16][CH2:15][CH2:14][CH2:13][N:12]2[CH:17]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 41097072-(2,4-Dichlorophenyl)imidazo[1,2-a]pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 22625614HCID 22625614, compoundYield 26.3%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

To 4.5 g (17.1 mmol) of the above 2-(2,4-dichlorophenyl)-imidazo[1,2-a]pyridine in a Paar bottle, 100 ml of ethanol, 1.5 ml of concentrated hydrochloric acid, and 0.4 g of platinum oxide were added. This mixture was placed on a Paar hydrogenator at 45 psi of hydrogen at room temperature for 15 minutes. Thin layer chromatography revealed that the reaction was complete. The mixture was filtered through celite and washed with 300 ml of ethyl acetate. To the filtrate, excess saturated aqueous sodium bicarbonate was slowly added. The ethyl acetate layer was separated, washed with saturated brine, and dried over magnesium sulfate. Evaporating the solvent in vacuo gave a solid residue to which n-butyl chloride was added. The solid was filtered, washed with n-butyl chloride, and dried to give 1.2 g of the title compound (m.p. 134-136° C.). The filtrate was also concentrated in vacuo to give a sludge which on silica gel chromatography (5:1 followed by 3:1 followed in turn by 1:1 hexane/ethyl acetate) afforded another 2.1 g of the title compound.

Workup

  1. filtrationThe mixture was filtered through celite
  2. washwashed with 300 ml of ethyl acetate
  3. additionTo the filtrate, excess saturated aqueous sodium bicarbonate was slowly added
  4. customThe ethyl acetate layer was separated
  5. washwashed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customEvaporating the solvent in vacuo
  8. customgave a solid residue to which n-butyl chloride
  9. additionwas added
  10. filtrationThe solid was filtered
  11. washwashed with n-butyl chloride
  12. customdried

Sources & evidence

ORD record
ord-3fe2aeb0a7084d45aed0f508fa961718
Source dataset
uspto-grants-2002_03
Patent number
US06358885B1

Reaction notes

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