2-Chlorophenylhydrazine hydrochloride → HCID 118431880, compound

HRID 2207928Notes

Reaction equation

HRID 2207928 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4](=O)[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=1[F:14].Cl.[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH:25][NH2:26]>C(O)(=O)C>[CH3:1][O:2][C:3]([C:4]1[CH2:5][CH:6]([C:7]2[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=2[F:14])[N:25]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[Cl:18])[N:26]=1)=[O:16]

Participants

4

Reactant 2

HCID 4432872-Chlorophenylhydrazine hydrochlorideHCID 131735959HCID 131735959, compound

Product 1

HCID 118431880HCID 118431880, compoundYield 104.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

4-(4-Bromo-2-fluoro-phenyl)-2-oxo-3-butenoic acid methyl ester (2.0 g, 7.0 mmol) prepared in Step 2 and 2-chlorophenylhydrazine hydrochloride (1.4 g, 7.7 mmol) were added to acetic acid (25.0 mL). The reaction mixture was stirred at 80° C. for 2 hours, concentrated under reduced pressure, and then ethyl acetate was added thereto. The mixture was washed with a saturated solution of sodium hydrogen carbonate, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give 3.0 g of the titled compound as a black liquid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionethyl acetate was added
  3. washThe mixture was washed with a saturated solution of sodium hydrogen carbonate
  4. dry with materialdried on anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-30396475ce1a48c3952f8a5a4d7afab5
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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