3-Bromophenylhydrazine hydrochloride → HCID 57428254, compound

HRID 733133Notes

Reaction equation

HRID 733133 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([NH:9][NH2:10])[CH:6]=[CH:7][CH:8]=1.[CH2:11]([O:13][C:14](=[O:22])[C:15](=[CH:18]OCC)[C:16]#[N:17])[CH3:12].C([O-])(=O)C.[Na+]>C(O)(=O)C.O>[NH2:17][C:16]1[C:15]([C:14]([O:13][CH2:11][CH3:12])=[O:22])=[CH:18][N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([Br:2])[CH:4]=2)[N:10]=1

Participants

6

Reactant 3

HCID 337573-Bromophenylhydrazine hydrochlorideHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 517045Sodium Acetate

Product 1

HCID 57428254HCID 57428254, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 3-bromophenylhydrazine hydrochloride (2.25 g, 10.1 mmol) in acetic acid (15.1 mL) and water (5.04 mL) were added ethyl(ethoxymethylene)cyanoacetate (1.88 g, 11.1 mmol) and sodium acetate (3.02 g, 22.2 mmol), and the solution was refluxed for 16 hours. The reaction was cooled and quenched with ice-water. The precipitate formed was filtered, washed with water and dried under vacuum for 24 hours to give 2.95 g of the titled compound (93% yield).

Workup

  1. temperaturethe solution was refluxed for 16 hours
  2. temperatureThe reaction was cooled
  3. customquenched with ice-water
  4. customThe precipitate formed
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried under vacuum for 24 hours

Sources & evidence

ORD record
ord-33dbe6dcf7804c28bc97e1cb88d6002c
Source dataset
uspto-grants-2009_09
Patent number
US07589116B2

Reaction notes

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