Dichloromethane → 1-(2-Methylphenyl)-6-methylpyrrolo[3,2-c]cinnoline

HRID 704573Notes

Reaction equation

HRID 704573 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([CH3:21])[C:14]=3[N:13]=[N:12][C:11]=2[CH2:10][CH2:9]1.ClCCl>C1(OC2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)Cl.[Pd]>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([CH3:21])[C:14]=3[N:13]=[N:12][C:11]=2[CH:10]=[CH:9]1

Participants

6

Reactant 2

HCID 6344DichloromethaneHCID 200727571-(2-Methylphenyl)-6-methyl-2,3-dihydropyrrolo [3,2-c]cinnoline

Product 1

HCID 200727541-(2-Methylphenyl)-6-methylpyrrolo[3,2-c]cinnoline

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6212ChloroformSolvent2×HCID 7583Diphenyl EtherSolvent

Procedure

To a refluxing slurry of 10% Pd/C (0.4 g) in diphenyl ether (20 ml) was added 1-(2-methylphenyl)-6-methyl-2,3-dihydropyrrolo [3,2-c]cinnoline (1.25 g, 0.0045 mol). After 0.5 hour at reflux temperature the reaction mixture was cooled, diluted with chloroform and the catalyst was filtered off over hyflo. The product was isolated by column chromatography using dichloromethane (11) then chloroform. The oil obtained was crystallized from ethyl acetate, 0.42 g, m.p. 105-106°.

Workup

  1. temperatureAfter 0.5 hour at reflux temperature the reaction mixture
  2. temperaturewas cooled
  3. filtrationthe catalyst was filtered off over hyflo
  4. customThe product was isolated by column chromatography
  5. customThe oil obtained
  6. customwas crystallized from ethyl acetate, 0.42 g, m.p. 105-106°

Sources & evidence

ORD record
ord-c6ddbe0469dc4c2e99913a8c9ed2a0f2
Source dataset
uspto-grants-1991_01
Patent number
US04988695

Reaction notes

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