3-Bromophenylhydrazine hydrochloride → HCID 118431728, compound

HRID 2207954Notes

Reaction equation

HRID 2207954 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:19]=[C:20]([NH:24][NH2:25])[CH:21]=[CH:22][CH:23]=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:20]2[CH:21]=[CH:22][CH:23]=[C:18]([Br:17])[CH:19]=2)[N:25]=1)=[O:15]

Participants

4

Reactant 2

HCID 337573-Bromophenylhydrazine hydrochlorideHCID 77141723HCID 77141723, compound

Product 1

HCID 118431728HCID 118431728, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
125 °C

Procedure

4-(2-Chloro-phenyl)-2-oxo-3-butenoic acid methyl ester (1.4 g, 6.0 mmol) prepared in Step 2 of Preparation 24 and 3-bromophenylhydrazine hydrochloride (1.4 g, 6.1 mmol) were added to acetic acid (20.0 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 methanol to give 1.2 g of the titled compound as a pale yellow 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 methanol

Sources & evidence

ORD record
ord-d942b4b8d75242aa8d03b785f07842b6
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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