Sodium Iodide → HCID 53392179, compound

HRID 1922370Notes

Reaction equation

HRID 1922370 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][CH:19]1[CH2:23][CH2:22][CH2:21][N:20]1[CH3:24].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH3:24][N:20]1[CH2:21][CH2:22][CH2:23][CH:19]1[CH2:18][CH2:17][N:10]1[C:11]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:13][CH:12]=2)[CH2:7][CH2:8][C:9]1=[O:14]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 3017050Pyrrolidine, 2-(2-chloroethyl)-1-methyl-, hydrochloride (1:1)HCID 51117496-Nitro-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 53392179HCID 53392179, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 6-nitro-3,4-dihydroquinolin-2(1H)-one (2.0 g, 10.4 mmol), 2-(2-chloroethyl)-1-methylpyrrolidine hydrochloride (3.83 g, 20.8 mmol), sodium iodide (779 mg, 5.20 mmol) and potassium carbonate (8.63 g, 62.4 mmol) in dimethylformamide (15 mL) was stirred at room temperature overnight. After this time, the mixture was diluted with water (15 mL) then extracted with ethyl acetate (3×75 mL). The combined organic fractions were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was subjected to flash chromatography on silica gel using 5% 2M NH3 in MeOH/CH2Cl2 to give an orange oil which solidified upon drying under reduced pressure (2.32 g, 73.7%). 1H-NMR (CDCl3) δ: 8.13 (dd, J=2.7, 9 Hz, 1H), 8.05 (d, J=2.4 Hz, 1H), 7.11 (d, J=9.0 Hz, 1H), 4.15-4.05 (m, 1H), 3.97-3.87 (m, 1H), 3.05-3.01 (m, 4H), 2.72-2.70 (m, 2H), 2.28 (s, 3H), 2.17-1.60 (m, 7H).

Workup

  1. extractionthen extracted with ethyl acetate (3×75 mL)
  2. washThe combined organic fractions were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an orange oil which
  7. customupon drying under reduced pressure (2.32 g, 73.7%)

Sources & evidence

ORD record
ord-d34807334ae24fca94e2a38c009bf225
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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