O-Toluidine → HCID 54029568, compound

HRID 1419867Notes

Reaction equation

HRID 1419867 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][S:19][CH2:20][CH2:21][CH3:22])(=[O:4])[CH2:2][CH3:3].[NH2:23][C:24]1[C:25]([CH3:30])=[CH:26][CH:27]=[CH:28][CH:29]=1>C(#N)C>[C:1]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH3:30])=[CH:12][CH:11]=[CH:10][C:9]=2[O:16][CH2:17][CH2:18][S:19][CH2:20][CH2:21][CH3:22])(=[O:4])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 54378137HCID 54378137, compound

Product 1

HCID 54029568HCID 54029568, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Propanoyl-4-chloro-8-(2-propylthioethoxy)quinoline (2.5 g, 7.40 mmol) and o-toluidine (0.95 g, 8.86 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 crude product was purified by column chromatography (methylene chloride:ethyl acetate 80:20). 1.8 g (60%) 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 crude product was purified by column chromatography (methylene chloride:ethyl acetate 80:20)

Sources & evidence

ORD record
ord-3a80b571c464448b9715eac2064f3dc8
Source dataset
uspto-grants-1999_03
Patent number
US05889021

Reaction notes

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