Sodium Hydroxide → HCID 86755204, compound

HRID 1636380Notes

Reaction equation

HRID 1636380 reaction equation
[CH2:1]([N:3]([CH2:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([CH2:17][O:18][NH:19][C:20]([C:22]1[CH:30]=[CH:29][C:25]([C:26]([OH:28])=O)=[CH:24][CH:23]=1)=[O:21])[CH:11]=[CH:10]2)[CH2:4][CH3:5])[CH3:2].S(Cl)([Cl:33])=O.Cl.[NH2:36][OH:37].C(=O)(O)[O-].[Na+].[OH-].[Na+]>C(Cl)(Cl)Cl.O.C1COCC1>[ClH:33].[CH2:4]([N:3]([CH2:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([CH2:17][O:18][NH:19][C:20]([C:22]1[CH:23]=[CH:24][C:25]([C:26]([NH:36][OH:37])=[O:28])=[CH:29][CH:30]=1)=[O:21])[CH:11]=[CH:10]2)[CH2:1][CH3:2])[CH3:5]

Participants

9

Reactant 5

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 19351111HCID 19351111, compound

Product 1

HCID 86755204HCID 86755204, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-[6-(diethylaminomethyl)naphth-2-ylmethyloxycarbamoyl]benzoic acid (13.1 g, 32 mmol) and thionyl chloride (7 ml, 96 mmol) in chloroform (300 ml) was refluxed for 4 hours, then the solvent and thionyl chloride were evaporated. Crude was dissolved in chloroform (100 ml) and evaporated to dryness three times. Crude was added as solid to a solution of hydroxylamine hydrochloride (2.7 g, 39 mmol) and sodium bicarbonate (5.4 g, 64 mmol) and 1N sodium hydroxide (39 ml, 39 mmol) in water (150 ml) and THF (50 ml). The mixture was stirred overnight at room temperature, then THF was removed under reduced pressure and the aqueous phase was extracted with ethyl acetate (3×100 ml). The combined organic phases were dried over anhydrous sodium sulphate and the solvent was removed under reduced pressure. Crude was dissolved in THF and treated with a 1.5 N etheric solution of HCl. The solid product was filtered and dried yielding 6 g (yield 41%) of pure 4-[6-(diethylaminomethyl)naphth-2-ylmethyloxycarbamoyl]benzohydroxamic acid hydrochloride as white solid; m.p.=162-165° C., (dec.)

Workup

  1. customthe solvent and thionyl chloride were evaporated
  2. dissolutionCrude was dissolved in chloroform (100 ml)
  3. customevaporated to dryness three times
  4. customTHF was removed under reduced pressure
  5. extractionthe aqueous phase was extracted with ethyl acetate (3×100 ml)
  6. dry with materialThe combined organic phases were dried over anhydrous sodium sulphate
  7. customthe solvent was removed under reduced pressure
  8. dissolutionCrude was dissolved in THF
  9. additiontreated with a 1.5 N etheric solution of HCl
  10. filtrationThe solid product was filtered
  11. customdried

Sources & evidence

ORD record
ord-e8c1ff20e98d491f955158ab783a5d31
Source dataset
uspto-grants-2000_03
Patent number
US06034096

Reaction notes

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