Triethylamine → HCID 9614877, compound

HRID 584344Notes

Reaction equation

HRID 584344 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 acetate-hexane 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 acetate-hexane

Sources & evidence

ORD record
ord-30c6bd70e7b04c11b6a80e01d5518e4b
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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