Hydrochloric Acid → HCID 178515608, compound

HRID 612940Notes

Reaction equation

HRID 612940 reaction equation
[OH-:1].[Na+].Cl.[NH2:4]O.C([O:8][C:9](=O)[C:10](Br)=[C:11](Br)[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)C.Cl>CO.O1CCOCC1.O>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]2[O:1][N:4]=[C:9]([OH:8])[CH:10]=2)=[CH:13][CH:14]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 54157979HCID 54157979, compound

Product 1

HCID 178515608HCID 178515608, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydroxide (151 g) was dissolved in methanol (600 ml), and an aqueous hydroxylamine hydrochloride (45 g) solution (50 ml) was added dropwise thereto under stirring at 0° C., and then a solution of α,β-dibromo-4-chlorocinnamic acid ethyl ester (200 g) in dioxane (200 ml) was added dropwise to the mixture. The resulting mixture was stirred at room temperature for 4 hours and further refluxed for 5 hours. The reaction mixture was cooled to 5° C., and the pH of the mixture was adjusted to a value of 2 with conc. hydrochloric acid. Then, the reaction mixture was added to water (5 L). Precipitate was separated from the mixture by filtration and washed with water (2 L) and then with ethanol (1 L) to obtain 90 g of the title compound (85%) as a pale yellow powder.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 4 hours
  2. temperaturefurther refluxed for 5 hours
  3. temperatureThe reaction mixture was cooled to 5° C.
  4. customPrecipitate was separated from the mixture by filtration
  5. washwashed with water (2 L)

Sources & evidence

ORD record
ord-db298345ae46478fada4593e2231abf0
Source dataset
uspto-grants-1999_12
Patent number
US06005116

Reaction notes

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