1-(2-Methylphenyl)-4-chloro-6-methyl-2,3-dihydropyrrolo[3,2-c]quinoline → 1-(2-Methylphenyl)-6-methyl-2,3-dihydropyrrolo[3,2-c]quinoline

HRID 729089Notes

Reaction equation

HRID 729089 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]=[C:12](Cl)[C:11]=2[CH2:10][CH2:9]1>C(O)C.[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]=[CH:12][C:11]=2[CH2:10][CH2:9]1

Participants

4

Reactant 1

HCID 157498191-(2-Methylphenyl)-4-chloro-6-methyl-2,3-dihydropyrrolo[3,2-c]quinoline

Product 1

HCID 157498241-(2-Methylphenyl)-6-methyl-2,3-dihydropyrrolo[3,2-c]quinolineYield 31%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-(2-Methylphenyl)-4-chloro-6-methyl-2,3-dihydropyrrolo[3,2-c]quinoline (1.5 g) in ethanol (100 ml) was hydrogenated over 10% palladium on charcoal (0 25 g) at an initial pressure of 3 bar. After 7 hours the mixture was filtered through celite and evaporated. Conversion to free base and recrystallisation from ethyl acetate/petroleum ether yielded 1-(2-methylphenyl)-6-methyl-2,3-dihydropyrrolo[3,2-c]quinoline (0.11 g, 31%), m.p. 109°-110°.

Workup

  1. filtrationAfter 7 hours the mixture was filtered through celite
  2. customevaporated
  3. customConversion to free base and recrystallisation from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-8e288e35df4b4d26a9fb3049ec23b48f
Source dataset
uspto-grants-1991_09
Patent number
US05051508

Reaction notes

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