Water → HCID 15728701, compound

HRID 1886258Notes

Reaction equation

HRID 1886258 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O-:8])=O.CN([CH:15]=[O:16])C.[C:17](Cl)(=O)[C:18](Cl)=O.C([N:25]([CH2:28][CH3:29])CC)C.OS([O-])(=O)=O.[K+].[OH2:36]>C1COCC1.C(Cl)Cl>[OH:36][N:25]([C:28]1[CH:29]=[CH:18][C:17]2[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=2)[C:15]=1[OH:16])[C:6](=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2][C:1]([O:10][CH3:11])=[O:9]

Participants

9

Reactant 6

HCID 962WaterHCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 516920Potassium bisulfateHCID 6994472Methyl adipate

Product 1

HCID 15728701HCID 15728701, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Into a 25 ml methylene chloride solution of 500 mg (3.12 mmol) of monomethyl adipate and 240 μl (3.12 mmol) of DMF was added 613 μl (7.02 mmol) of oxalyl chloride at 0° C., and the mixture was stirred as such for one hour. The mixture was then added to a solution of 3.4 g (16 mmol) of 1-hydroxy-2-naphthylhyiroxylamine hydrochloride, 3.3 ml (24 mmol) of triethylamine in THF (25 ml), and water (5 ml), at 0° C., and after stirring at 0° C. for one hour and at room temperature for one hour, the reaction was completed with aqueous KHSO4, and the mixture was extracted with methylene chloride. The organic layer was washed with 4N HCl and then with saturated aqueous NaCl, and dried over anhydrous magnesium sulfate, and after evaporation of the solvent under a reduced pressure, the residue was subjected to silica gel column chromatography to give 762 mg (77%) of the desired product.

Workup

  1. stirringafter stirring at 0° C. for one hour and at room temperature for one hour
  2. extractionthe mixture was extracted with methylene chloride
  3. washThe organic layer was washed with 4N HCl
  4. dry with materialwith saturated aqueous NaCl, and dried over anhydrous magnesium sulfate
  5. customafter evaporation of the solvent under a reduced pressure

Sources & evidence

ORD record
ord-595e41ed5c1c490daf203e692d4b3a6d
Source dataset
uspto-grants-1992_09
Patent number
US05149859

Reaction notes

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