Sodium hydride → HCID 14209221, compound

HRID 1646866Notes

Reaction equation

HRID 1646866 reaction equation
[H-].[Na+].Br[C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][OH:17])=[CH:11][CH:10]=[C:9]([Cl:18])[CH:8]=2>CN(C=O)C.O>[Cl:18][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[NH:14][CH2:15][CH2:16][O:17][C:4]=3[CH:5]=[N:6][C:7]=2[CH:8]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 14209236HCID 14209236, compound

Product 1

HCID 14209221HCID 14209221, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (obtained from 3 g of 50% suspension in mineral oil) was added to a solution of 3-bromo-7-chloro-N-(2-hydroxyethyl)-4-quinolinamine (15 g) in 30 ml of DMF and the mixture stirred at 80°-90° C. for 2 hours. After cooling, it was diluted with 300 ml of water and the product extracted with ethyl acetate. The extract was dried over sodium sulfate, the solvent was evaporated and the oily residue purified by high pressure liquid chromatography (HPLC) (hexane:ethyl acetate=1:1). The desired fractions were combined, concentrated and recrystallized from isopropanol. The yield was 2.0 g, mp 219°-220° C.

Workup

  1. temperatureAfter cooling
  2. extractionthe product extracted with ethyl acetate
  3. dry with materialThe extract was dried over sodium sulfate
  4. customthe solvent was evaporated
  5. customthe oily residue purified by high pressure liquid chromatography (HPLC) (hexane:ethyl acetate=1:1)
  6. concentrationconcentrated
  7. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-0710d1fc599741d58c2b7946899ec2e0
Source dataset
uspto-grants-1993_01
Patent number
US05182275

Reaction notes

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