4-Bromophenylhydrazine hydrochloride → HCID 118432002, compound

HRID 2207951Notes

Reaction equation

HRID 2207951 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4](=O)[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:13].Cl.[Br:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][NH2:25])=[CH:20][CH:19]=1>C(O)(=O)C>[CH3:1][O:2][C:3]([C:4]1[CH2:5][CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:13])[N:24]([C:21]2[CH:22]=[CH:23][C:18]([Br:17])=[CH:19][CH:20]=2)[N:25]=1)=[O:15]

Participants

4

Reactant 2

HCID 121574-Bromophenylhydrazine hydrochlorideHCID 77141723HCID 77141723, compound

Product 1

HCID 118432002HCID 118432002, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
125 °C

Procedure

4-(2-Chloro-phenyl)-2-oxo-3-butenoic acid methyl ester (4.9 g, 21.9 mmol) prepared in Step 2 and 4-bromophenylhydrazine hydrochloride (5.0 g, 22.4 mmol) was added to acetic acid (50.0 mL). The reaction mixture was stirred at 125° C. for 3 hours, concentrated under reduced pressure, and then ethyl acetate was added thereto. The reaction mixture was washed with a saturated solution of sodium hydrogen carbonate, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting yellow liquid residue was crystallized from diethyl ether to give 5.3 g of the titled compound as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionethyl acetate was added
  3. washThe reaction mixture was washed with a saturated solution of sodium hydrogen carbonate
  4. dry with materialdried on anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a yellow liquid residue
  7. customThe resulting yellow liquid residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-d8f660bfefb04e32ba7e5a99ff6c60c7
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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