HCID 67900102, compound → HCID 19913140, compound

HRID 1091161Notes

Reaction equation

HRID 1091161 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[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1)=[O:18]>CO.[Pd]=O>[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][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[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1)=[O:18]

Participants

4

Reactant 1

HCID 67900102HCID 67900102, compound

Product 1

HCID 19913140HCID 19913140, compound

Reagents, catalysts & solvents 2

HCID 5083724Palladium monoxideCatalystHCID 887MethanolSolvent2×

Procedure

A suspension of (E)-3-(5-methyl-1H-imidazol-4-yl)-1-(1-naphthalenyl)-2-propen-1-one maleate (0.38 g) in methanol (50 ml) was hydrogenated at room temperature and atmospheric pressure over a stirred suspension of pre-reduced 10% palladium oxide on carbon (50% aqueous paste; 40 mg) in methanol (10 ml) for 2 h. The reaction mixture was filtered, the filtrate was concentrated in vacuo to ca. 5 ml, and diluted with dry ether (ca. 150 ml) to precipitate the title compound (0.28 g) as a solid, m.p. 107°-108°.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo to ca. 5 ml
  4. additiondiluted with dry ether (ca. 150 ml)
  5. customto precipitate the title compound (0.28 g) as a solid, m.p. 107°-108°

Sources & evidence

ORD record
ord-66ffdc4a1ac743cdb1390cafda2fa34a
Source dataset
uspto-grants-1992_01
Patent number
US05084474

Reaction notes

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