Sodium hydride → HCID 17956066, compound

HRID 2103204Notes

Reaction equation

HRID 2103204 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[CH3:13].[H-].[Na+].[Cl:16][CH2:17][CH2:18][CH2:19]I>CN(C=O)C>[Cl:16][CH2:17][CH2:18][CH2:19][N:9]1[C:10]2[C:5](=[CH:4][C:3]([CH3:13])=[C:2]([F:1])[CH:11]=2)[CH2:6][CH2:7][C:8]1=[O:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 813631-Chloro-3-iodopropaneHCID 17956177HCID 17956177, compound

Product 1

HCID 17956066HCID 17956066, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A reaction flask was charged with 7-fluoro-6-methyl-3,4-dihydro-1H-quinolin-2-one (97KK40) (0.102 g, 0.57 mmol) in dry DMF (5 mL) under an argon atmosphere. Washed NaH (0.015 g, 0.63 mmol) was added and the mixture was stirred at rt for 1 h. Then 1-chloro-3-iodopropane (0.104 g, 0.51 mmol) dissolved in DMF (1 mL) was added followed by stirring at rt for 20 h. The reaction mixture was quenched with water, and the product extracted into Et2O. The combined organic layers were washed with aqueous 4% MgSO4, dried over Na2SO4, filtered, and concentrated. The product was purified by flash CC (SiO2; DCM/n-heptane 2:1, DCM, MeOH/DCM 1:10) to give the title compound (112KK01) (0.050 g, 38%). 1H NMR (CDCl3) δ 6.95-6.93 (m, 1H), 6.73 (d, J=11.5 Hz, 1H), 4.03-4.00 (m, 2H), 3.59 (t, J=6.5 Hz, CH2), 2.83-2.79 (m, 2H), 2.62-2.58 (m, 2H), 2.20 (d, J=1.8 Hz, CH3), 2.13-2.07 (m, 2H).

Workup

  1. additionwas added
  2. stirringby stirring at rt for 20 h
  3. customThe reaction mixture was quenched with water
  4. extractionthe product extracted into Et2O
  5. washThe combined organic layers were washed with aqueous 4% MgSO4
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe product was purified by flash CC (SiO2; DCM/n-heptane 2:1, DCM, MeOH/DCM 1:10)

Sources & evidence

ORD record
ord-48e7ece861574540ba1a9fd9359aa385
Source dataset
uspto-grants-2009_08
Patent number
US07576100B2

Reaction notes

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