O-Toluidine → 3-Butyryl-4-(2-methylphenylamino)-8-(2-methylthioethoxy)quinoline

HRID 743103Notes

Reaction equation

HRID 743103 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][S:20][CH3:21])(=[O:5])[CH2:2][CH2:3][CH3:4].[NH2:22][C:23]1[C:24]([CH3:29])=[CH:25][CH:26]=[CH:27][CH:28]=1>C(#N)C>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29])=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH2:18][CH2:19][S:20][CH3:21])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 545624293-Butyryl-4-chloro-8-(2-methylthioethoxy)quinoline

Product 1

HCID 539093553-Butyryl-4-(2-methylphenylamino)-8-(2-methylthioethoxy)quinoline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 3-butyryl-4-chloro-8-(2-methylthioethoxy)quinoline (0.67 g, 2.1 mmol) and o-toluidine (0.24 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 saturated sodium bicarbonate solution. The organic layer was dried over sodium sulfate and evaporated. The residue was triturated with diisopropylether. The precipitated product was filtered off and washed with diisopropyl ether giving 0.55 g (66%) 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
  5. customThe residue was triturated with diisopropylether
  6. filtrationThe precipitated product was filtered off
  7. washwashed with diisopropyl ether giving 0.55 g (66%) of the title compound

Sources & evidence

ORD record
ord-6a4beebfca60485da98e80619d6f9568
Source dataset
uspto-grants-1996_09
Patent number
US05556863

Reaction notes

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