2-Bromoethanol → 2-[(2-Amino-4-quinolinyl)oxy]-1-ethanol

HRID 991655

Reaction equation

HRID 991655 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([OH:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:20][CH2:21][OH:22]>CN(C=O)C>[NH2:1][C:2]1[CH:11]=[C:10]([O:12][CH2:20][CH2:21][OH:22])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 178507928HCID 178507928, compound

Product 1

HCID 220365112-[(2-Amino-4-quinolinyl)oxy]-1-ethanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 2-amino-4-hydroxyquinoline (0.505 g, 3.15 mmol) and K2CO3 (0.87 g, 6.3 mmol) in DMF (10 mL) was added of 2-bromoethanol (0.470 g, 3.78 mmol). The mixture was stirred at 150° C. for 7 h. The reaction mixture was concentrated and the residue purified by column chromatography on silica using MeOH/CHCl3 (1:9) as eluent. The resulting brown oil (0.30 g, 30%), which was used directly in the next step, contained 75% of the desired product and 25% of unreacted starting material. MS m/z 205 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue purified by column chromatography on silica

Sources & evidence

ORD record
ord-469c3147585c474ba85d8e37252a6e68
Source dataset
uspto-grants-2002_10
Patent number
US06465467B1

Linked notes

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