Hydrochloric Acid → HCID 21437949, compound

HRID 2397386Notes

Reaction equation

HRID 2397386 reaction equation
O.Cl.C1(C)C=CC=CC=1.[C:10]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26](=O)[CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[CH:22][CH:21]=2)=[CH:16][C:15]=1[Br:33])(=[O:12])[CH3:11]>[Zn].O1CCOCC1>[C:10]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[CH:22][CH:21]=2)=[CH:16][C:15]=1[Br:33])(=[O:12])[CH3:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 1140TolueneHCID 21437911HCID 21437911, compound

Product 1

HCID 21437949HCID 21437949, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 312751,4-DioxaneSolvent

Procedure

7.5 ml of water, 17.5 ml of concentrated hydrochloric acid, 50 ml of toluene, 30 ml of dioxane and 5 gm of 4-(4'-acetamido-3'-bromo-4-biphenylyl)-4-oxo-butyric acid were added to 10 gm of amalgamated zinc. This reaction mixture was refluxed for 4 hours. After standing overnight at room temperature, the precipitated crystals were collected and recrystallized from ethyl acetate. Yield: 35% of theory; m.p. 155°-156° C. Melting point of the cyclohexylamine salt: 179°-180° C. (precipitated from ethyl acetate).

Workup

  1. temperatureThis reaction mixture was refluxed for 4 hours
  2. customthe precipitated crystals were collected
  3. customrecrystallized from ethyl acetate
  4. customMelting point of the cyclohexylamine salt: 179°-180° C. (precipitated from ethyl acetate)

Sources & evidence

ORD record
ord-8836d309797c4426ae6ee72469c1ffcd
Source dataset
uspto-grants-1977_05
Patent number
US04021479

Reaction notes

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