HCID 20463284, compound → HCID 20463331, compound

HRID 325944Notes

Reaction equation

HRID 325944 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[C:7](=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14].[H][H]>C(O)(=O)C.[Pd]>[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14]

Participants

5

Reactant 2

HCID 20463284HCID 20463284, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 20463331HCID 20463331, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

2.1 g of 5-methyl-4-(2'-methylbenzoyl)imidazole are dissolved in 10 ml of acetic acid. 0.2 g of 10% palladium-on-carbon is added and the reaction mixture is agitated vigorously at about 60° C. in a hydrogen atmosphere until the uptake of hydrogen ceases. The mixture is then cooled and filtered and the filtrate is evaporated to dryness. The residue is dissolved in 20 ml of water and the resultant solution is made alkaline (pH about 10) with sodium hydroxide. The precipitate which forms is removed by filtration, washed with water and dried. The product is transformed to the hydrochloride in isopropanol, its melting point after recrystallization from water-ethanol being 226°-268° C. The free base, 5-methyl-4-(2'-methylbenzyl)imidazole, which is liberated from the hydrochloride in water with sodium hydroxide, has a melting point of 138°-140° C.

Workup

  1. temperatureThe mixture is then cooled
  2. filtrationfiltered
  3. customthe filtrate is evaporated to dryness
  4. dissolutionThe residue is dissolved in 20 ml of water
  5. customThe precipitate which forms is removed by filtration
  6. washwashed with water
  7. customdried
  8. customafter recrystallization from water-ethanol being 226°-268° C

Sources & evidence

ORD record
ord-8ade4dafb36a43ea9ebf79b0c8006bcc
Source dataset
uspto-grants-1984_04
Patent number
US04443466

Reaction notes

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