Triethylamine → HCID 9614877, compound

HRID 2299703Notes

Reaction equation

HRID 2299703 reaction equation
[C:1]1([C:7](=O)[C:8]([O:10][CH3:11])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:14][OH:15].C(N(CC)CC)C>CO>[OH:15]/[N:14]=[C:7](\[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)/[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 84835Methyl phenylglyoxalateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 9614877HCID 9614877, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl phenylglyoxylate (25.5 g), hydroxylamine hydrochloride (11.3 g), triethylamine (22.8 ml) and methanol (300 ml) was stirred for 17 hours at 60° C. The reaction mixture was concentrated, and the residue was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, (MgSO4), and then concentrated. The residual crystals were recrystallized from ethyl acetatehexane to obtain methyl E-2-hydroxyimino-2-phenylacetate (3.58 g, yield 13%) as colorless crystals. m.p. 151-153° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water, (MgSO4),
  5. concentrationconcentrated
  6. customThe residual crystals were recrystallized from ethyl acetatehexane

Sources & evidence

ORD record
ord-5367eb70c379419a8de16972d4480ebc
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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