O-Toluidine → HCID 54548203, compound

HRID 743114Notes

Reaction equation

HRID 743114 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. (1H-NMR, 300 MHz, CDCl3) 0.94 (t, 3H), 1.26 (t, 3H), 1.57 (m, 2H), 2.25 (m, 2H), 2.34 (s, 3H), 2.49 (t, 2H), 2.75 (t, 2H), 3.15 (q, 2H), 4.27 (t, 2H) 6.83-7.23 (m, 7H), 9.22 (s, 1H), 11.73 (s, 1H).

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-2912cb9777b04734aad44f227aa2dce8
Source dataset
uspto-grants-1996_09
Patent number
US05556863

Reaction notes

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