Water → HCID 16073843, compound

HRID 1067975Notes

Reaction equation

HRID 1067975 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16](/[CH:21]=[CH:22]\[CH2:23][OH:24])=[CH:15][CH:14]=3)=[O:9])=[CH:4][CH:3]=1.[C:27]([O-])([O-])=O.[K+].[K+].IC.O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16](/[CH:21]=[CH:22]\[CH2:23][OH:24])[CH:17]=3)[N:12]([CH3:27])[CH:11]=2)=[O:9])=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178522860HCID 178522860, compound

Product 1

HCID 16073843HCID 16073843, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-(4-chlorobenzyl)-6-[(1Z)-3-hydroxy-1-propenyl]-4-hydroxy-3-quinolinecarboxamide from Preparation No. 11 (0.184 g), K2CO3 (0.276 g) and iodomethane (0.062 mL) in DMF (2 mL) is heated in a stoppered flask at 90° C. for 1 h. Water is added and the mixture is allowed to cool and stir at room temperature for 16 h during which a precipitate formed. The precipitate is filtered and dried in vacuo at 60° C. for 48 h to give a solid. Crystallization by dissolving in CH2Cl2 with a few drops of MeOH and adding to a 1:1 solution of pentane/Et2O gave 0.085 g of the title compound as a solid.

Workup

  1. customfrom Preparation No
  2. temperatureto cool
  3. customformed
  4. filtrationThe precipitate is filtered
  5. customdried in vacuo at 60° C. for 48 h
  6. customto give a solid
  7. customCrystallization
  8. dissolutionby dissolving in CH2Cl2 with a few drops of MeOH
  9. additionadding to a 1:1 solution of pentane/Et2O

Sources & evidence

ORD record
ord-f619146a126f4d2a845f2dea59e929af
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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