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

HRID 729096Notes

Reaction equation

HRID 729096 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][S-:24].[Na+]>CC(O)C>[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]([S:24][CH3:23])[C:11]=2[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 157498191-(2-Methylphenyl)-4-chloro-6-methyl-2,3-dihydropyrrolo[3,2-c]quinoline

Product 1

HCID 157498271-(2-Methylphenyl)-4-methylthio-6-methyl-2,3-dihydropyrrolo-[3,2-c]quinolineYield 49.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1-(2-Methylphenyl)-4-chloro-6-methyl-2,3-dihydro pyrrolo-[3,2-c]quinoline (1.54 g, 5 mmol) and sodium methanethiolate (1.40 g, 20 mmol) in 2-propanol (25 ml) were heated at 170° in a pressure vessel for 18 hours. The solvent was evaporated, the residue taken up in dichloromethaneand washed with sodium bicarbonate solution. Chromatography (silica gel, dichloromethane) and crystallisation from methanol gave 1-(2-methylphenyl)-4-methylthio-6-methyl-2,3-dihydropyrrolo-[3,2-c]quinoline (0.8 g), m.p. 111°-113°.

Workup

  1. customThe solvent was evaporated
  2. washwashed with sodium bicarbonate solution
  3. customChromatography (silica gel, dichloromethane) and crystallisation from methanol

Sources & evidence

ORD record
ord-75c23114dd3440799a55c2028a62fff4
Source dataset
uspto-grants-1991_09
Patent number
US05051508

Reaction notes

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