Ammonia → 8-(5-Methoxy-2-benzimidazolyl)thiomethyl-1-methyl-1,2,3,4-tetrahydroquinoline

HRID 1088814Notes

Reaction equation

HRID 1088814 reaction equation
Cl.[C:2]([S:5][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]([CH3:17])[CH2:14][CH2:13][CH2:12]2)(O)=O.[CH3:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([NH2:27])=[C:24]([NH2:26])[CH:25]=1.N>Cl>[CH3:18][O:19][C:20]1[CH:21]=[CH:22][C:23]2[N:27]=[C:2]([S:5][CH2:6][C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:16]=3[N:15]([CH3:17])[CH2:14][CH2:13][CH2:12]4)[NH:26][C:24]=2[CH:25]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 1534044-Methoxy-o-phenylenediamineHCID 221617698-Carboxythiomethyl-1-methyl-1,2,3,4-tetrahydroquinoline hydrochloride

Product 1

HCID 150533328-(5-Methoxy-2-benzimidazolyl)thiomethyl-1-methyl-1,2,3,4-tetrahydroquinolineYield 14.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

8-Carboxythiomethyl-1-methyl-1,2,3,4-tetrahydroquinoline hydrochloride (27.9 g) and 5-methoxy-o-phenylenediamine (13.8 g) in 4N hydrochloric acid (100 ml) were refluxed for 40 minutes. The reaction mixture was cooled, neutralized with aqueous ammonia and extracted with chloroform. After drying the extract, the solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography [eluent:n-hexane-ethyl acetate (4:1)] to give 8-(5-methoxy-2-benzimidazolyl)thiomethyl-1-methyl-1,2,3,4-tetrahydroquinoline (5.0 g).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with chloroform
  3. customAfter drying the extract
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography [eluent:n-hexane-ethyl acetate (4:1)]

Sources & evidence

ORD record
ord-62963d26e5244183968d03127117918c
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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