8-Hydroxyquinoline → HCID 61723548, compound

HRID 1777134Notes

Reaction equation

HRID 1777134 reaction equation
[H-].[Na+].[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[OH:13])[CH:6]=[CH:5][CH:4]=1.Br[CH:15]([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17]>CN(C=O)C.O>[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:13][CH:15]([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 19238-HydroxyquinolineHCID 24758Sodium hydrideHCID 79040Ethyl 2-bromopropionate

Product 1

HCID 61723548HCID 61723548, compoundYield 59.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of compound NaH (100 mg, 4.14 mmol) in DMF (3 mL) was added quinolin-8-ol (200 mg, 1.38 mmol) at 26° C. After stirred for 5 minutes, ethyl 2-bromopropanoate (300 mg, 1.65 mmol) was added and the reaction mixture stirred for 16 h at 26° C. The mixture was then diluted with water (20 mL) and extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with brine (20 mL), dried over Na2SO4 and concentrated to give ethyl 2-(quinolin-8-yloxy)propanoate (200 mg, 59.2%) as colorless oil which was used in next step without further purification. (304 mg, Yield 90%).

Workup

  1. stirringthe reaction mixture stirred for 16 h at 26° C
  2. extractionextracted with ethyl acetate (3×10 mL)
  3. washThe combined organic layers were washed with brine (20 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c6286a539a8a40f981ba43ba8a510ffc
Source dataset
uspto-grants-2016_02
Patent number
US09266836B2

Reaction notes

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