Dichloromethane → 3-Butyryl-4-(2-chlorophenylamino)-8-(2-methylthioethoxy)quinoline

HRID 743116Notes

Reaction equation

HRID 743116 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].[Cl:22][C:23]1[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=1[NH2:25].C(Cl)Cl.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.O>[CH:18]([O:17][CH:10]([CH3:9])[CH3:11])([CH3:19])[CH3:23].[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:25][C:24]1[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=1[Cl:22])=[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

8

Reactant 4

HCID 6344DichloromethaneHCID 72402-ChloroanilineHCID 516892Sodium BicarbonateHCID 545624293-Butyryl-4-chloro-8-(2-methylthioethoxy)quinoline

Product 2

HCID 7914Diisopropyl EtherHCID 544124113-Butyryl-4-(2-chlorophenylamino)-8-(2-methylthioethoxy)quinolineYield 161.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-butyryl-4-chloro-8-(2-methylthioethoxy)quinoline (0.8 g, 2.5 mmol) and 2-chloroaniline (0.47 g, 3.7 mmol) in toluene (12 ml) was heated to 90° C. and stirred 3.0 h. After cooling to room temperature, methylene chloride and water were added. The mixture was neutralized with a saturated solution of sodium bicarbonate. The organic layer was dried over sodium sulfate and evaporated. Trituration with isopropyl ether gave 0.84 g (81%) of the desired product.

Workup

  1. temperatureAfter cooling to room temperature
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-ac5dcc36700b46728f14bb20a926e9e3
Source dataset
uspto-grants-1996_09
Patent number
US05556863

Reaction notes

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