Hydrochloric Acid → HCID 136388365, compound

HRID 432050Notes

Reaction equation

HRID 432050 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[C:9]([O:11][CH3:12])=[O:10].Cl.[NH2:15][OH:16].O.Cl>CO>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[N:15][OH:16])[C:9]([O:11][CH3:12])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 182159Benzeneacetic acid, 2-hydroxy-alpha-oxo-, methyl esterHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 136388365HCID 136388365, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.3 g (0.016 mol) of methyl 2-hydroxyphenylglyoxylate (HPLC: 88%, log p=1.87) (Example VI-1a) and 1.3 g (0.019 mol) of hydroxylamine hydrochloride in 50 ml of methanol are heated under reflux for one hour. The reaction mixture is poured into water, acidified with 2N hydrochloric acid and extracted with diethyl ether, the organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure. This gives 2.4 g of crude product which, according to HPLC, contains 17.1% of methyl E-2-(2-hydroxyphenyl)-2-hydroxyimino-acetate of log p=0.95 and 68.9% of methyl Z-2-(2-hydroxyphenyl)-2-hydroxyimino-acetate of log p=1.68.

Workup

  1. temperatureunder reflux for one hour
  2. extractionextracted with diethyl ether
  3. dry with materialthe organic phase is dried over sodium sulphate
  4. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-7d7c40f548264478a0bd61370a77c91c
Source dataset
uspto-grants-2003_12
Patent number
US06660872B1

Reaction notes

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