HCID 54325121, compound → HCID 10471686, compound

HRID 486207Notes

Reaction equation

HRID 486207 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]1[C:11](=[O:41])[C:12](=[CH:15][C:16]3[N:17]=[CH:18][N:19](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C:20]=3[CH3:21])[CH2:13][CH2:14][C:6]1=[C:5]2[CH3:42]>C(O)(=O)C.[Zn]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]1[C:11](=[O:41])[CH:12]([CH2:15][C:16]3[N:17]=[CH:18][NH:19][C:20]=3[CH3:21])[CH2:13][CH2:14][C:6]1=[C:5]2[CH3:42]

Participants

4

Reactant 1

HCID 54325121HCID 54325121, compound

Product 1

HCID 10471686HCID 10471686, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 2-chloro-8,9-dihydro-10-methyl-7-[(5-methyl-1-trityl-1H-imidazol-4-yl)methylene]pyrido[1,2-a]indol-6(7H)-one (0.95 g) in acetic acid (47.5 ml) was added zinc powder (1.09 g) and the mixture was refluxed for 2.5 hours. The resulting precipitates were filtered off, and the filtrate was evaporated in vacuo. The residue was diluted in chloroform, washed with aqueous sodium bicarbonate, solution, water, and brine, dried over sodium sulfate, and chromatographed on silica gel eluted by chloroform-methanol (0-5% V/V), to give 2-chloro-8,9-dihydro-10-methyl-7-[(5-methyl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one (0.50 g).

Workup

  1. temperaturethe mixture was refluxed for 2.5 hours
  2. customThe resulting precipitates
  3. filtrationwere filtered off
  4. customthe filtrate was evaporated in vacuo
  5. additionThe residue was diluted in chloroform
  6. washwashed with aqueous sodium bicarbonate, solution, water, and brine
  7. dry with materialdried over sodium sulfate
  8. customchromatographed on silica gel
  9. washeluted by chloroform-methanol (0-5% V/V)

Sources & evidence

ORD record
ord-64f79073d5154ce6affb2326e526c27a
Source dataset
uspto-grants-1994_03
Patent number
US05290785

Reaction notes

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