Dichloromethane → HCID 53761935, compound

HRID 1419874Notes

Reaction equation

HRID 1419874 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].[CH3:22][O:23][C:24]1[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=1[NH2:26].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])[CH3:22].[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[O:23][CH3:22])=[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 70002-MethoxyanilineHCID 516892Sodium BicarbonateHCID 545624293-Butyryl-4-chloro-8-(2-methylthioethoxy)quinoline

Product 2

HCID 7914Diisopropyl EtherHCID 53761935HCID 53761935, compoundYield 155.9%

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-methoxyaniline (0.45 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 0.80 g (77%) 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-70737bcffd8d4ec6be031dea062d0b87
Source dataset
uspto-grants-1999_03
Patent number
US05889021

Reaction notes

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