O-Toluidine → HCID 54083198, compound

HRID 743129Notes

Reaction equation

HRID 743129 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH2:18][CH2:19][CH2:20][S:21][CH3:22])(=[O:5])[CH2:2][CH2:3][CH3:4].[CH3:23][C:24]1[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=1[NH2:26]>C1(C)C=CC=CC=1>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:26][C:25]1[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=1[CH3:23])=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH2:18][CH2:19][CH2:20][S:21][CH3:22])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 54199407HCID 54199407, compound

Product 1

HCID 54083198HCID 54083198, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 3-butyryl-4-chloro-8-(3-methylthiopropoxy)quinoline (0.95 g, 2.97 mmol) and 2-methylaniline (1.27 g, 11.8 mmol) in toluene was heated to 55° C. and stirred overnight. The solvent was evaporated and the residue was partioned between methylene chloride and a saturated sodium bicarbonate solution. The organic layer was dried over Na2SO4 and evaporated. The residue was chromatographed (SiO2 ; CH2Cl2MeOH 95:5) yielding 0.98 g (80.9%) of the desired product.

Workup

  1. customThe solvent was evaporated
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated
  4. customThe residue was chromatographed (SiO2 ; CH2Cl2MeOH 95:5)

Sources & evidence

ORD record
ord-6760f89590f947e199da6a9e133ff87d
Source dataset
uspto-grants-1996_09
Patent number
US05556863

Reaction notes

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