HCID 54433637, compound → HCID 10403682, compound

HRID 847516Notes

Reaction equation

HRID 847516 reaction equation
[CH2:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]2[C:13](=[O:43])[C:14](=[CH:17][C:18]3[N:19]=[CH:20][N:21](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C:22]=3[CH3:23])[CH2:15][CH2:16][C:5]=12)[CH:2]=[CH2:3]>C(O)(=O)C.[Zn]>[CH2:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]2[C:13](=[O:43])[CH:14]([CH2:17][C:18]3[N:19]=[CH:20][NH:21][C:22]=3[CH3:23])[CH2:15][CH2:16][C:5]=12)[CH:2]=[CH2:3]

Participants

4

Reactant 1

HCID 54433637HCID 54433637, compound

Product 1

HCID 10403682HCID 10403682, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 10-allyl-8,9-dihydro-7-[(5-methyl-1-trityl-1H-imidazol-4-yl)methylene]pyrido[1,2-a]indol-6(7H)-one and zinc powder (2.0 g) in acetic acid (30 ml) was stirred vigorously at 100° C. for 2 hours. Zinc powder (1.5 g) was added and the mixture was heated for further 1 hour. After being cooled to room temperature, the insoluble material was filtered and washed with acetic acid. After evaporation of the solvent, the residue was diluted with water and washed twice with toluene. The toluene layer was extracted with 0.5N hydrochloric acid. The combined aqueous layers were neutralized with aqueous sodium bicarbonate solution and extracted three times with chloroform. The chloroform layer was washed with water twice and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. Chromatography (silica gel, 5% methanol-chloroform) of the residue, followed by recrystallization from methanol-chloroform-hexane, gave 10-allyl-8,9-dihydro-7-[(5-methyl-1H-imidazol-4-yl)-methyl]pyrido[1,2-a]indol-6(7H)-one (0.63 g).

Workup

  1. temperaturethe mixture was heated for further 1 hour
  2. temperatureAfter being cooled to room temperature
  3. filtrationthe insoluble material was filtered
  4. washwashed with acetic acid
  5. customAfter evaporation of the solvent
  6. additionthe residue was diluted with water
  7. washwashed twice with toluene
  8. extractionThe toluene layer was extracted with 0.5N hydrochloric acid
  9. extractionextracted three times with chloroform
  10. washThe chloroform layer was washed with water twice
  11. dry with materialbrine, dried over anhydrous magnesium sulfate
  12. customevaporated in vacuo
  13. customChromatography (silica gel, 5% methanol-chloroform) of the residue, followed by recrystallization from methanol-chloroform-hexane

Sources & evidence

ORD record
ord-891e73ce37a0471abbcbc3fc7335b74c
Source dataset
uspto-grants-1992_08
Patent number
US05141945

Reaction notes

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