O-Toluidine → HCID 53940201, compound

HRID 743107Notes

Reaction equation

HRID 743107 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][CH3:20])(=[O:4])[CH2:2][CH3:3].[NH2:21][C:22]1[C:23]([CH3:28])=[CH:24][CH:25]=[CH:26][CH:27]=1>C(#N)C>[C:1]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH3:28])=[CH:12][CH:11]=[CH:10][C:9]=2[O:16][CH2:17][CH2:18][S:19][CH3:20])(=[O:4])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 54113854HCID 54113854, compound

Product 1

HCID 53940201HCID 53940201, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 3-propanoyl-4-chloro-8-(2-methylthioethoxy)quinoline (0.60 g, 1.9 mmol) and o-toluidine (0.25 g, 2.3 mmol) in acetonitrile was heated to 55° C. and stirred for 3.5 h. The solvent was evaporated and the residue was partitioned between methylene chloride and a 10% sodium carbonate solution. The organic layer was dried over sodium sulfate and evaporated. Chromatography (SiO2 ; CH2Cl2 :EtOAc 60:40) gave 0.45 g (61%) of the title compound.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between methylene chloride
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-ee88ed7261fa4ca698b4609f944e22c7
Source dataset
uspto-grants-1996_09
Patent number
US05556863

Reaction notes

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