Sodium Iodide → HCID 67916452, compound

HRID 1030269Notes

Reaction equation

HRID 1030269 reaction equation
CNC[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:16](=[O:19])([O-])[O-].[K+].[K+].ClCCC[C:26]1[CH:31]=[C:30]([N+:32]([O-:34])=[O:33])[CH:29]=[CH:28][C:27]=1[O:35][C:36]1C=CC([N+]([O-])=O)=[CH:38][C:37]=1CCCCl.[C:49](#[N:51])C>>[N+:32]([C:30]1[CH:31]=[CH:26][C:27]([O:35][CH2:36][CH2:37][CH2:38][O:19][CH2:16][NH:51][CH2:49][N:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:12]=[CH:13][CH2:4]2)=[CH:28][CH:29]=1)([O-:34])=[O:33]

Participants

6

Reactant 5

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 15675896N-Methyl-1-(quinolin-2-yl)methanamineHCID 86745673HCID 86745673, compound

Product 1

HCID 67916452HCID 67916452, compoundYield 36%

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 3-chloropropyl-4-nitrophenyl ether (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% MeOH/CH2Cl2) 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% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-3a662e6248ba4e818e986b13d525305e
Source dataset
uspto-grants-1992_04
Patent number
US05104892

Reaction notes

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