HCID 67900236, compound → HCID 67900143, compound

HRID 2051574Notes

Reaction equation

HRID 2051574 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[CH3:9][C:10]1[NH:14][CH:13]=[N:12][C:11]=1/[CH:15]=[CH:16]/[C:17]([C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=1)=[O:18]>CO.[Pd]=O>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[CH3:9][C:10]1[NH:14][CH:13]=[N:12][C:11]=1[CH2:15][CH2:16][C:17]([C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=1)=[O:18]

Participants

4

Reactant 1

HCID 67900236HCID 67900236, compound

Product 1

HCID 67900143HCID 67900143, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 5083724Palladium monoxideCatalystHCID 887MethanolSolvent2×

Procedure

A solution of (E)-3-(5-methyl-1H-imidazol-4-yl)-1-(2-naphthalenyl)-2-propen-1one maleate (300 mg) in hot methanol (90 ml) was hydrogenated at room temperature and atmospheric pressure over a stirred suspension of pre-reduced 10% palladium oxide on carbon (50% aqueous paste; 30 mg) in methanol (10 ml) for 16 h. The suspension was filtered, evaporated in vacuo, and the residual oil (ca. 350 mg) was partitioned between dichloromethane (3×50 ml) and 2N sodium carbonate (50 ml). The combined organic extracts were dried and evaporated in vacuo. The residual oil (300 mg) was dissolved in absolute ethanol (6 ml) and treated with a solution of maleic acid (100 mg) in ethanol (1 ml). Dilution with dry ether (ca. 75 ml) afforded the title compound (210 mg) as a solid, m.p. 137°-138°, t.l.c. (System A, 89:10:1) Rf 0.33.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe suspension was filtered
  3. customevaporated in vacuo
  4. customthe residual oil (ca. 350 mg) was partitioned between dichloromethane (3×50 ml) and 2N sodium carbonate (50 ml)
  5. customThe combined organic extracts were dried
  6. customevaporated in vacuo
  7. dissolutionThe residual oil (300 mg) was dissolved in absolute ethanol (6 ml)
  8. additiontreated with a solution of maleic acid (100 mg) in ethanol (1 ml)

Sources & evidence

ORD record
ord-5f618c0878084fccbf236ef3843380c6
Source dataset
uspto-grants-1991_05
Patent number
US05019586

Reaction notes

Loading…