2-Chloroquinoline → HCID 15177820, compound

HRID 1939879Notes

Reaction equation

HRID 1939879 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH:8]2[CH:17]([OH:18])[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([OH:19])[CH:15]=3)[O:10][CH2:9]2)[CH:2]=1.Cl[C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1.[H-].[Na+]>CN(C)C=O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C@H:8]2[C@@H:17]([OH:18])[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:19][C:21]4[CH:30]=[CH:29][C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[N:22]=4)[CH:15]=3)[O:10][CH2:9]2)[CH:2]=1

Participants

5

Reactant 3

HCID 119282-ChloroquinolineHCID 24758Sodium hydrideHCID 15181191HCID 15181191, compound

Product 1

HCID 15177820HCID 15177820, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(3-Pyridylmethyl)-4,6-chromandiol (5.0 g, 19.4 mmol; EP appln. 312,295) was dissolved in 100 ml dimethylformamide. 2-Chloroquinoline (3.17 g, 19.4 mmol) and then NaH (0.98 g of a 50% dispersion in oil, 20.4 mmol) were added and the mixture stirred at 90°-95° C. for 16 hours. The reaction mixture was cooled, quenched into 500 ml H2O, and extracted 4×400 ml ethyl acetate. The organic layers were combined, washed 3×400 ml H2O and 1×400 ml brine, dried (Na2 SO4), stripped to an oil (9.47 g) and chromatographed in silica gel gradiently eluted with 4-15% CH3OH in CH2Cl2 to yield 5.07 g of present title product as a white foam; IR (KBr) 3190, 1602, 1492 cm-1 ; MS 384 (M+).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customquenched into 500 ml H2O
  3. extractionextracted 4×400 ml ethyl acetate
  4. washwashed 3×400 ml H2O and 1×400 ml brine
  5. customdried (Na2 SO4)
  6. customchromatographed in silica gel
  7. washgradiently eluted with 4-15% CH3OH in CH2Cl2

Sources & evidence

ORD record
ord-f280de8ecec146698ea67dd412aa8726
Source dataset
uspto-grants-1997_12
Patent number
US05698550

Reaction notes

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