O-Toluidine → HCID 54548203, compound

HRID 1419869Notes

Reaction equation

HRID 1419869 reaction equation
[C:1]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1Cl)=[CH:12][CH:11]=[CH:10][C:9]=2[O:16][CH2:17][CH2:18][CH2:19][S:20][CH2:21][CH2:22][CH3:23])(=[O:4])[CH2:2][CH3:3].[NH2:24][C:25]1[C:26]([CH3:31])=[CH:27][CH:28]=[CH:29][CH:30]=1>C(#N)C>[C:1]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH3:31])=[CH:12][CH:11]=[CH:10][C:9]=2[O:16][CH2:17][CH2:18][CH2:19][S:20][CH2:21][CH2:22][CH3:23])(=[O:4])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 54337959HCID 54337959, compound

Product 1

HCID 54548203HCID 54548203, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Propanoyl-4-chloro-8-(3-propylthiopropoxy)quinoline (2.0 g, 5.7 mmol) and o-toluidine (0.7 g, 6.5 mmol) was refluxed in acetonitrile (10 ml) for 2 h. The solvent was evaporated and the residue was partitioned between methylene chloride and 10% Na2CO3 solution. The organic layer was dried over Na2SO4 and evaporated. The residue was purified by column chromatography (methylene chloride:ethyl acetate 70:30). 1.3 g (54%) of the title compound was obtained.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between methylene chloride and 10% Na2CO3 solution
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated
  5. customThe residue was purified by column chromatography (methylene chloride:ethyl acetate 70:30)

Sources & evidence

ORD record
ord-c061741411c04305a9702efbb4c461eb
Source dataset
uspto-grants-1999_03
Patent number
US05889021

Reaction notes

Loading…