Salicylhydroxamic Acid → HCID 178518983, compound

HRID 1293114Notes

Reaction equation

HRID 1293114 reaction equation
[C:1]([NH:10][OH:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)O.C(N1C=CN=C1)(N1C=CN=C1)=O>C1COCC1>[O:11]1[C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1]([OH:9])=[N:10]1

Participants

4

Reactant 2

HCID 66644Salicylhydroxamic AcidHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 178518983HCID 178518983, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of salicylhydroxamic acid (1.53 g, 10 mmol) in THF (40 ml) was added a solution of carbonyldiimidazole (1.62 g, 20 mmol) in tetrahydrofuran (20 ml). The mixture was stirred at reflux for 4 hrs. before evaporation to dryness. Water (20 ml) and conc. HCl (aq.) (5 ml) were added and the solution was refrigerated (5° C.) for 30 min. The resulting precipitate was collected by filtration and washed with 2M HCl. The solid material was dissolved in methanol and concentrated in vacuo yielding 725 mg (54%) of the title compound 71. TLC (10% methanol in DCM): Rf=0.2. HPLC-MS (Method A): M+=136.1 (UV/MS(%)=94/100). 1H-NMR (400 MHz, CDCl3, MeOD): δ=7.73 (1H, m); 7.56 (1H, m); 7.38 (1H, m); 7.28 (1H, m); 3.87 (1H, s).

Workup

  1. temperatureat reflux for 4 hrs
  2. custombefore evaporation to dryness
  3. additionWater (20 ml) and conc. HCl (aq.) (5 ml) were added
  4. custom(5° C.)
  5. customfor 30 min
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with 2M HCl
  8. dissolutionThe solid material was dissolved in methanol
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-247c532ac1564a71bbf72373153a7681
Source dataset
uspto-grants-2007_07
Patent number
US07238713B2

Reaction notes

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