Sodium hydride → HCID 22987165, compound

HRID 2304568Notes

Reaction equation

HRID 2304568 reaction equation
[CH2:1]([C:3]1([C:9]2[CH:14]=[CH:13][NH:12][C:11](=[O:15])[CH:10]=2)[O:8][CH2:7][CH2:6][CH2:5][O:4]1)[CH3:2].[H-].[Na+].Br[CH2:19][C:20]1[C:21]([Cl:30])=[N:22][C:23]2[C:28]([CH:29]=1)=[CH:27][CH:26]=[CH:25][CH:24]=2>O1CCCC1.[Cl-].[NH4+]>[Cl:30][C:21]1[C:20]([CH2:19][N:12]2[CH:13]=[CH:14][C:9]([C:3]3([CH2:1][CH3:2])[O:4][CH2:5][CH2:6][CH2:7][O:8]3)=[CH:10][C:11]2=[O:15])=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 13593314HCID 13593314, compoundHCID 22987160HCID 22987160, compound

Product 1

HCID 22987165HCID 22987165, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

A solution under argon of 4-(2-ethyl-1,3-dioxan-2-yl)-1,2-dihydro-2-pyridinone (obtained according to 4.e, 11 g, 52 mmol) in anhydrous tetrahydrofuran (370 ml) is treated at 0° C. with sodium hydride (80% in mineral oil, 1.68 g, 56 mmol). The resulting mixture is maintained under agitation at 0° C. for 15 min then treated with 3-bromomethyl-2-chloroquinoline (obtained according to 4.b, 13.4 g, 52 mmol) and the resulting mixture is maintained under agitation at ambient temperature for 24 hours. The reaction medium is then poured into an aqueous solution saturated in ammonium chloride (400 ml), the phases are separated, and the aqueous phase aqueuse is extracted with dichloromethane. The combined organic phases are washed with saturated aqueous sodium chloride, dried over magnesium sulphate and concentrated under reduced pressure. The residue taken up in diethyl ether forms a precipitate which is collected by filtration and dried in order to produce 13.8 g (69%) of a white solid.

Workup

  1. temperaturethe resulting mixture is maintained under agitation at ambient temperature for 24 hours
  2. customthe phases are separated
  3. extractionthe aqueous phase aqueuse is extracted with dichloromethane
  4. washThe combined organic phases are washed with saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure
  7. filtrationis collected by filtration
  8. customdried in order

Sources & evidence

ORD record
ord-dc4e01c4e2a54009a8aabae478f76e9f
Source dataset
uspto-grants-2002_08
Patent number
US06436951B1

Reaction notes

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