HCID 178477924, compound → HCID 178419888, compound

HRID 1017742Notes

Reaction equation

HRID 1017742 reaction equation
Cl[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][CH:7]2[C:12]1[N:13]=[CH:14][NH:15][CH:16]=1>C(O)C.[Pd]>[CH:7]1([C:12]2[N:13]=[CH:14][NH:15][CH:16]=2)[C:8]2[C:3](=[CH:2][CH:11]=[CH:10][CH:9]=2)[CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 178477924HCID 178477924, compound

Product 1

HCID 178419888HCID 178419888, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-(5-Chloro-1,2,3,4-tetrahydronaphthalen-1-yl)-1H-imidazole (300 mg) is dissolved in ethanol (15 ml). The reaction solution is hydrogenated at 50° C. with 10% palladium on carbon as catalyst for 8 hours. The mixture is filtered to remove the catalyst, and the filtrate is evaporated under reduced pressure. The residue is dissolved in water and is made alkaline with sodium hydroxide solution. The product is extracted into methylene chloride which is washed with water, dried with sodium sulfate and evaporated under reduced pressure. The crude product is recrystallized from ethyl acetate. The yield is 169 mg, m.p. 105-110° C.

Workup

  1. filtrationThe mixture is filtered
  2. customto remove the catalyst
  3. customthe filtrate is evaporated under reduced pressure
  4. dissolutionThe residue is dissolved in water
  5. extractionThe product is extracted into methylene chloride which
  6. washis washed with water
  7. dry with materialdried with sodium sulfate
  8. customevaporated under reduced pressure
  9. customThe crude product is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f03130d0bfda4e6b836b01f313174c06
Source dataset
uspto-grants-2002_11
Patent number
US06479530B2

Reaction notes

Loading…