Pyridine → HCID 54260928, compound

HRID 649551Notes

Reaction equation

HRID 649551 reaction equation
[Br:1][CH2:2][C:3](=[N:9][OH:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[Cl:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](Cl)=[O:17])=[CH:14][CH:13]=1.N1C=CC=CC=1>C(Cl)Cl>[Br:1][CH2:2][C:3](=[N:9][O:10][C:16](=[O:17])[C:15]1[CH:19]=[CH:20][C:12]([Cl:11])=[CH:13][CH:14]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 85014-Chlorobenzoyl chlorideHCID 53428735Ethyl 3-bromo-2-(hydroxyimino)propanoate

Product 1

HCID 54260928HCID 54260928, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the mixture of ethyl 3-bromo-2-(hydorxyimino)propanoate (3 g, 14.3 mmole) and 4-chlorobenzoyl chloride (2.75 g, 15.71 mmole) in dry methylene chloride (100 ml) at 0° to 5° C. with stirring, was slowly added dry pyridine (1.2 g, 15.18 mmole). After addition, the reaction mixture was stirred at room temperature for one hour. The reaction mixture was diluted with 50 ml of methylene chloride and washed with water and brine. The organic layer was dried with magnesium sulfate and the solvent evaporated to afford 5.0 g (99% yield) of ethyl 3-bromo-2-(4-chlorobenzoyloximino)propanoate as a white solid, m.p. 82°-84.5° C.

Workup

  1. additionAfter addition
  2. stirringthe reaction mixture was stirred at room temperature for one hour
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-094be155489742378374e2a059873718
Source dataset
uspto-grants-1988_04
Patent number
US04740524

Reaction notes

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