Water → HCID 69203919, compound

HRID 2215458Notes

Reaction equation

HRID 2215458 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]([NH:7][CH2:8][CH3:9])[CH3:6].CO[C:12]([C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[NH2:24])[N:15]=1)=[O:13].O>C1(C)C=CC=CC=1>[CH2:5]([N:7]([CH2:8][CH3:9])[C:12]([C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[NH2:24])[N:15]=1)=[O:13])[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 8021DiethylamineHCID 6451240Aluminum(III) ChlorideHCID 45089604Methyl 5-aminoquinoline-2-carboxylate

Product 1

HCID 69203919HCID 69203919, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

A suspension that consists of 1.06 g (7.95 mmol) of aluminum chloride in 35 ml of toluene is mixed with 1.70 ml (15.7 mmol) of diethylamine while being cooled with ice. After one hour at room temperature, 350 mg (1.73 mmol) of 5-aminoquinoline-2-carboxylic acid methyl ester is added, and the reaction mixture is allowed to stir for 5 hours at 40° C. The reaction is halted by adding water. It is extracted with dichloromethane, and the combined organic phases are dried on sodium sulfate. After removal of the solvent and purification on silica gel with dichloromethane-methanol (0-10%), 210 mg (50% of theory) of the product is obtained.

Workup

  1. temperaturewhile being cooled with ice
  2. extractionIt is extracted with dichloromethane
  3. customthe combined organic phases are dried on sodium sulfate
  4. customAfter removal of the solvent and purification on silica gel with dichloromethane-methanol (0-10%), 210 mg (50% of theory) of the product
  5. customis obtained

Sources & evidence

ORD record
ord-bbfcc7b126af43ddbbf90e4a032c5a04
Source dataset
uspto-grants-2006_09
Patent number
US07109212B2

Reaction notes

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