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

HRID 729090Notes

Reaction equation

HRID 729090 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.[CH3:23][O-:24].[Na+]>CO>[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]([O:24][CH3:23])[C:11]=2[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 157498191-(2-Methylphenyl)-4-chloro-6-methyl-2,3-dihydropyrrolo[3,2-c]quinoline

Product 1

HCID 157498261-(2-Methylphenyl)-4-methoxy-6-methyl-2,3-dihydropyrrolo-[3,2-c]quinolineYield 49.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(2-Methylphenyl)-4-chloro-6-methyl-2,3-dihydropyrrolo[3,2-c]quinoline (0.62 g, 2 mmol), sodium methoxide (1.0 g, 18.5 mmol) and methanol (30 ml)were heated to 170° C. in a pressure vessel for 18 hours, then the solvent evaporated in vacuo. Conversion to free base, chromatography (silica gel. 40:60 dichloromethane/petroleum ether) and recrystallisation from methanol yielded 1-(2-methylphenyl)-4-methoxy-6-methyl-2,3-dihydropyrrolo- [3,2-c]quinoline(0.30 g), m.p. 107°-108°.

Workup

  1. customthe solvent evaporated in vacuo
  2. customConversion to free base, chromatography (silica gel. 40:60 dichloromethane/petroleum ether) and recrystallisation from methanol

Sources & evidence

ORD record
ord-a4bc2989854d4296928d8ba54182bdf1
Source dataset
uspto-grants-1991_09
Patent number
US05051508

Reaction notes

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