Methyl iodide → HCID 178488573, compound

HRID 30438Notes

Reaction equation

HRID 30438 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[C:14]([OH:21])[CH:15]=[CH:16][CH:17]=3)[N:12]=2)=[NH:10])=[CH:4][CH:3]=1.[C:22]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[C:14]([O:21][CH3:22])[CH:15]=[CH:16][CH:17]=3)[N:12]=2)=[NH:10])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178512015HCID 178512015, compound

Product 1

HCID 178488573HCID 178488573, compoundYield 45.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 0.10 g (0.33 mmol) of N-(4-chloro-phenyl)-8-hydroxy -quinoline-2-carboxamidine, 0.137 g (1 mmol) of K2CO3 and 0.021 g (0.33 mmol) of iodomethane in 3.5 mL of DMF was heated under microwave (100 W, 5 min). It was diluted with 20 mL of NaHCO3, extracted with three 10 mL portions of ether. The combined organic extracts were washed with 10 mL of brine, dried over Na2SO4, filtered and concentrated. The residue was purified by preparative TLC eluting with 20% ethyl acetate in hexanes to give 0.047 g of N-(4-chloro-phenyl)-8-methoxy -quinoline-2-carboxamidine.

Workup

  1. temperaturewas heated under microwave (100 W, 5 min)
  2. extractionextracted with three 10 mL portions of ether
  3. washThe combined organic extracts were washed with 10 mL of brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by preparative TLC
  8. washeluting with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-e3d414a4cd0c472e9a59e9d630c15676
Source dataset
uspto-grants-2008_09
Patent number
US07423149B2

Reaction notes

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