Hydrochloric Acid → 4-(4'-Amino-3'-bromo-4-biphenylyl)-butyric acid

HRID 2397385Notes

Reaction equation

HRID 2397385 reaction equation
O.Cl.C1(C)C=CC=CC=1.[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23](=O)[CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:19][CH:18]=2)=[CH:13][C:12]=1[Br:30]>[Zn].O1CCOCC1>[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:21][CH:22]=2)=[CH:13][C:12]=1[Br:30]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 1140TolueneHCID 214379204-(4'-Amino-3'-bromo-4-biphenylyl)-4-oxo-butyric acid

Product 1

HCID 214379264-(4'-Amino-3'-bromo-4-biphenylyl)-butyric acidYield 25%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6 ml of water, 8 gm of amalgamated zinc, 14 ml of concentrated hydrochloric acid, 20 ml of toluene and 4 gm of 4-(4'-amino-3'-bromo-4-biphenylyl)-4-oxo-butyric acid was refluxed for 6 hours, while stirring. Subsequently, 10 ml of dioxane were added and the toluene/dioxane phase was separated. The residue remaining after evaporation of the solvent was admixed with water, covered with ether, and adjusted with sodium bicarbonate solution to pH 6. The ether solution was separated, washed with water, dried over sodium sulfate and evaporated. The thus obtained 4-(4'-amino-3'-bromo-4-biphenylyl)-butyric acid was dissolved in ethyl acetate and converted into its cyclohexylamine salt by addition of cyclohexylamine. Yield: 25% of theory. Melting point of the cyclohexylamine salt: 182° C. (decomp.).

Workup

  1. temperaturewas refluxed for 6 hours
  2. customthe toluene/dioxane phase was separated
  3. customafter evaporation of the solvent
  4. customThe ether solution was separated
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. dissolutionThe thus obtained 4-(4'-amino-3'-bromo-4-biphenylyl)-butyric acid was dissolved in ethyl acetate
  9. additionconverted into its cyclohexylamine salt by addition of cyclohexylamine

Sources & evidence

ORD record
ord-44dc21cd8d8d4e199a16aa895484e535
Source dataset
uspto-grants-1977_05
Patent number
US04021479

Reaction notes

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