Sodium Iodide → HCID 19592750, compound

HRID 613584Notes

Reaction equation

HRID 613584 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[NH:15][CH:14]=[C:13]([CH2:17][O:18][CH3:19])[C:12]2=[O:20])=[O:5].Cl.Cl[CH2:28][C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN1CCCC1=O>[Cl:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][C:13]([CH2:17][O:18][CH3:19])=[C:12]2[O:20][CH2:28][C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1)=[O:5]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 19592484HCID 19592484, compound

Product 1

HCID 19592750HCID 19592750, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 8-(2,6-dichlorobenzoylamino)-1,4-dihydro-3-methoxymethyl-4-oxoquinoline (209 mg) in N-methylpyrrolidone (4 ml) were added 3-chloromethylpyridine hydrochloride (109 mg), potassium carbonate (153 mg) and sodium iodide (20 mg), and the mixture was stirred for 4 hours at 80° C. The mixture was partitioned between ethyl acetate and water, and the separated organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from ethanol to give 8-(2,6-dichlorobenzoylamino)-3-methoxymethyl-4-(pyridin-3-ylmethoxy)quinoline (170 mg) as white crystal.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washthe separated organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-2ca14d9716714760b7962417f310ec89
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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