Sodium hydride → HCID 16782057, compound

HRID 2103201Notes

Reaction equation

HRID 2103201 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]1=[O:11].[H-].[Na+].[Cl:14][CH2:15][CH2:16][CH2:17]I>CN(C=O)C>[Cl:14][CH2:15][CH2:16][CH2:17][N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]1=[O:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 64796HydrocarbostyrilHCID 813631-Chloro-3-iodopropane

Product 1

HCID 16782057HCID 16782057, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A 50 mL flask was charged with 3,4-dihydro-1H-quinolin-2-one (2.00 g, 13.6 mmol) and sodium hydride (60% in oil, 0.712 g, 16.3 mmol) in DMF (50 mL, dry) and stirred at 0° C. for 1 h, followed by addition of 1-chloro-3-iodo-propane (2.77 g, 13.6 mmol) and stirring at rt for 20 h. The reaction mixture was quenched with water (10 mL), and the product was extracted into EtOEt (3×25 mL). The combined organic layers were dried (Na2SO4), evaporated and purified by flash CC (SiO2; EtOAc/heptane 1:4) to give the crude title compound (85LM31) (2.25 g). 1H NMR (CDCl3) δ 7.29-7.22 (m, 1H), 7.17 (d, J=7.4 Hz, 1H), 7.08-6.98 (m, 2H), 4.10 (t, J=7.3 Hz, CH2), 3.62 (t, J=5.9 Hz, CH2), 2.88 (t, J=7.3 Hz, CH2), 2.63 (t, J=7.3 Hz, CH2), 2.19-2.10 (m, 2H); 13C NMR (CDCl3) δ 170.5, 140.0, 128.2, 127.8, 126.3, 123.2, 115.0, 43.3, 40.2, 32.2, 30.5, 26.0.

Workup

  1. stirringstirring at rt for 20 h
  2. customThe reaction mixture was quenched with water (10 mL)
  3. extractionthe product was extracted into EtOEt (3×25 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. customevaporated
  6. custompurified by flash CC (SiO2; EtOAc/heptane 1:4)

Sources & evidence

ORD record
ord-ee1cdda9c3674e88b9ea5e44fc63ed8a
Source dataset
uspto-grants-2009_08
Patent number
US07576100B2

Reaction notes

Loading…