Sodium Iodide → HCID 15675906, compound

HRID 1091081Notes

Reaction equation

HRID 1091081 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[N+:22]([C:25]1[CH:35]=[CH:34][C:28]([O:29][CH2:30][CH2:31][CH2:32]Cl)=[CH:27][CH:26]=1)([O-:24])=[O:23]>C(#N)C>[N+:22]([C:25]1[CH:35]=[CH:34][C:28]([O:29][CH2:30][CH2:31][CH2:32][N:2]([CH2:3][C:4]2[CH:13]=[CH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH3:1])=[CH:27][CH:26]=1)([O-:24])=[O:23]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 118446171-(3-Chloropropoxy)-4-nitrobenzeneHCID 15675896N-Methyl-1-(quinolin-2-yl)methanamine

Product 1

HCID 15675906HCID 15675906, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred suspension of 2-(methylaminomethyl)quinoline, prepared by the procedure of Example 3, Step 1, (3.67 g, 21.35 mmol), sodium iodide (2.78 g, 18.56 mmol), and potassium carbonate (3.08 g, 138.21 mmol) in acetonitrile (80 mL) was added 1-(4-nitrophenoxy)-3-chloropropane (4.00 g, 18.56 mmol). The mixture was stirred at 80° C. overnight, concentrated and partitioned between 10% K2CO3 and ethyl acetate. The organic phase was washed with brine, dried (MgSO4), and concentrated to afford an oil. The product was purified by HPLC (10% methanol/dichloromethane) to afford 2.34 g (36%) of pure product as a yellow oil.

Workup

  1. concentrationconcentrated
  2. custompartitioned between 10% K2CO3 and ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto afford an oil
  7. customThe product was purified by HPLC (10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-feddf5b7f945464e8c8129b28cc99084
Source dataset
uspto-grants-1992_01
Patent number
US05084463

Reaction notes

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