Water → 2-Methylquinoline

HRID 1604556Notes

Reaction equation

HRID 1604556 reaction equation
BrCC(NCC(N(C1C(Cl)=C(C(Cl)=CC=1)CO[C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[C:23]([CH3:26])[CH:22]=[CH:21]2)C)=O)=O.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:26][C:23]1[CH:22]=[CH:21][C:20]2[C:25](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:24]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 19603254HCID 19603254, compound

Product 1

HCID 70602-MethylquinolineYield 114.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 8-[3-[N-(bromoacetylglycyl)-N-methylamino]-2,6-dichlorobenzyloxy]-2-methylquinoline (80 mg) 5-amino-1,3,4-thiadiazole-2-thiol (24 mg), potassium carbonate (42 mg) in dimethylformamide (2 ml) was stirred for 30 minutes at ambient temperature. To the mixture was added water, and the mixture was extracted with ethyl acetate twice. Combined organic layers were washed with water three times, dried over magnesium sulfate and concentrated. The residue was pulverized from diethyl ether to give 8-[3-[N-(5-amino-1,3,4-thiadiazol-2-ylthio)acetylglycol]-N-methylamino]-2,6-dichlorobenzyloxy]-2-methylquinoline (25 mg) as a solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate twice
  2. washCombined organic layers were washed with water three times
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9acc7a1466e441ddb312d010121f4834
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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