Sodium Iodide → 1-(2-morpholinoethyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one

HRID 1922500Notes

Reaction equation

HRID 1922500 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8][CH2:7]2)([O-:3])=[O:2].Cl.Cl[CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[O:22]1[CH2:23][CH2:24][N:19]([CH2:18][CH2:17][N:10]2[C:11]3[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:13][CH:12]=3)[CH2:7][CH2:8][C:9]2=[O:14])[CH2:20][CH2:21]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 51117496-Nitro-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 598070771-(2-morpholinoethyl)-6-nitro-3,4-dihydroquinolin-2(1H)-oneYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 6-nitro-3,4-dihydroquinolin-2(1H)-one (1.00 g, 5.20 mmol), 4-(2-chloroethyl)morpholine hydrochloride (1.94 g, 10.40 mmol), sodium iodide (390 mg, 2.61 mmol) and potassium carbonate (4.32 g, 31.3 mmol) in DMF (5 mL) was stirred at room temperature for 60 hours. The mixture was transferred to a separatory funnel, diluted with water (45 mL) then extracted with ethyl acetate (3×35 mL). The combined organic fractions were washed with brine, dried (Na2SO4), filtered and concentrated. The crude product was subject to flash chromatography on silica gel using 2.5% 2M NH3 methanol/CH2Cl2, which resulted in a yellow solid, compound 2 (0.9211 g, 58%).

Workup

  1. customThe mixture was transferred to a separatory funnel
  2. extractionthen extracted with ethyl acetate (3×35 mL)
  3. washThe combined organic fractions were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-79e4e8e7c4134c5bb3808ca3b138abd7
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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