Water → HCID 178521499, compound

HRID 1858139Notes

Reaction equation

HRID 1858139 reaction equation
[OH:1][CH2:2][CH2:3][O:4][N:5]=[C:6]1[C:10](=O)[C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[O:7]1.Cl.[NH2:17][OH:18].O>CN1CCCC1=O>[OH:1][CH2:2][CH2:3][O:4][N:5]=[C:6]1[C:10](=[N:17][OH:18])[C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[O:7]1

Participants

5

Reactant 3

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 54464037Benzofuran-2,3-dione2-[o-(2-hydroxy-ethyl)-oxime]

Product 1

HCID 178521499HCID 178521499, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

At 80° C., 10.1 g (0.05 mol) of benzofuran-2,3-dione 2-[O-(2-hydroxy-ethyl)-oxime] (VII-1) in 50 ml of N-methyl-2-pyrrolidinone are stirred with 3.5 g of hydroxylamine hydrochloride for 2 hours. The reaction mixture is poured into water and the resulting mixture is extracted with ethyl acetate, the organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure. The residue is then chromatographed over silica gel using tert-butyl methyl ether/petroleum ether (1:1). The eluent is distilled off under reduced pressure, affording 4.2 g (29.6% of theory) of benzofuran-2,3-dione 2-[O-(2-hydroxy-ethyl)-oxime] 3-oxime consisting of 62.4% of isomer A and 15.8% of isomer B (HPLC).

Workup

  1. extractionthe resulting mixture is extracted with ethyl acetate
  2. dry with materialthe organic phase is dried over sodium sulphate
  3. distillationthe solvent is distilled off under reduced pressure
  4. customThe residue is then chromatographed over silica gel
  5. distillationThe eluent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-77776e705126493b8fb6e8fdaffc09bc
Source dataset
uspto-grants-2000_11
Patent number
US06150521

Reaction notes

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