Pyridine → HCID 131721733, compound

HRID 1637006Notes

Reaction equation

HRID 1637006 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=O)[C:13]([NH2:15])=[O:14])(=[O:3])[CH3:2].Cl.[CH3:18][O:19]N.C1(C)C=CC=CC=1.[N:28]1C=CC=CC=1>C(OCC)(=O)C>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]([O:19][CH3:18])[C:13]([N:15]=[NH:28])=[O:14])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 1140TolueneHCID 521874O-Methylhydroxylamine hydrochlorideHCID 19350201HCID 19350201, compound

Product 1

HCID 131721733HCID 131721733, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(2-acetoxymethylphenyl)-2-oxoacetamide (776 mg), O-methylhydroxylamine hydrochloride (439 mg), toluene (7.0 ml) and pyridine (3.5 ml) was stirred at 80° C. for 2 hours. After the reaction mixture was cooled by allowing it to stand, the reaction mixture was diluted with ethyl acetate, washed successively with 1N hydrochloric acid, water, saturated brine, and dried over anhydrous sodium sulfate. Evaporation of the solvent under reduced pressure gave the crude product (830 mg). This crude product was purified by column chromatography on silica gel to obtain the title compound (793 mg, yield: 90.3%, pale yellow crystals) as a mixture of the E- and Z-isomers (E/Z=56/44 determined by 1H-NMR analysis).

Workup

  1. temperatureAfter the reaction mixture was cooled
  2. washwashed successively with 1N hydrochloric acid, water, saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customEvaporation of the solvent under reduced pressure
  5. customgave the crude product (830 mg)
  6. customThis crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-1a8e676d14f048a4b5d4f8d02f73d0eb
Source dataset
uspto-grants-2000_03
Patent number
US06037495

Reaction notes

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