Potassium Carbonate → HCID 21192582, compound

HRID 1068048Notes

Reaction equation

HRID 1068048 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][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]([I:21])=[CH:15][CH:14]=3)=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=C(C)C=C(C)C=1S(O[NH2:42])(=O)=O>CN(C=O)C>[NH2:42][N:12]1[C:13]2[C:18](=[CH:17][C:16]([I:21])=[CH:15][CH:14]=2)[C:19](=[O:20])[C:10]([C:8]([NH:7][CH2:6][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:23][CH:22]=2)=[O:9])=[CH:11]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamineHCID 178522879HCID 178522879, compound

Product 1

HCID 21192582HCID 21192582, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of N-(4-chlorobenzyl)-4-hydroxy-6-iodo-3-quinolinecarboxamide (2.0 g) of Preparation No. 4 and of potassium carbonate (2.0 g) in DMF (40 mL) is stirred at room temperature for 5 hrs and then treated with of O-(mesitylsulfonyl)hydroxylamine (1.5 g). After 24 hrs, the solvent is evaporated under reduced pressure and the residue is diluted with water(150 mL). The resulting solid is filtered and washed with water (3×) and ether (2×). Recrystallization from hot acetic acid/water affords 1.35 g of the title compound as a tan solid.

Workup

  1. customthe solvent is evaporated under reduced pressure
  2. additionthe residue is diluted with water(150 mL)
  3. filtrationThe resulting solid is filtered
  4. washwashed with water (3×) and ether (2×)
  5. customRecrystallization from hot acetic acid/water

Sources & evidence

ORD record
ord-9c052d243c2448f1af0576a63a32754b
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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