HCID 20026416, compound → HCID 19769838, compound

HRID 1723295Notes

Reaction equation

HRID 1723295 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:16])[C:11]1[CH2:10][CH2:9]/[C:8](=[CH:17]\[C:18]3[N:19]=[CH:20][NH:21][C:22]=3[CH3:23])/[C:7](=[O:24])[C:6]2=1>C(O)C.[Pd]=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:16])[C:11]1[CH2:10][CH2:9][CH:8]([CH2:17][C:18]3[N:19]=[CH:20][NH:21][C:22]=3[CH3:23])[C:7](=[O:24])[C:6]2=1

Participants

4

Reactant 1

HCID 20026416HCID 20026416, compound

Product 1

HCID 19769838HCID 19769838, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 5083724Palladium monoxideCatalystHCID 702EthanolSolvent2×

Procedure

A solution of (E)-1,2,3,9-tetrahydro-6-methoxy-9-methyl-3-[(5-methyl-1H-imidazol-4-yl)methylene]-4H-carbazol-4-one (200 mg) in absolute ethanol (15 ml) was hydrogenated at room temperature and atmospheric pressure over a stirred suspension of 10% palladium oxide on carbon catalyst (50% aqueous paste; 100 mg) in absolute ethanol (5 ml). The mixture was filtered and evaporated to give a foam (ca. 200 mg) which was purified by FCC eluting with System A (200:10:1) to give the title compound (154 mg) as a solid, m.p. 227°-229°, t.l.c. (System A 200:10:1) RF 0.26.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe mixture was filtered
  3. customevaporated

Sources & evidence

ORD record
ord-ee386829930d422db96450bcff810185
Source dataset
uspto-grants-1989_08
Patent number
US04859662

Reaction notes

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