Pyridine → p-Iodobenzoic acid phenylhydrazide

HRID 328531Notes

Reaction equation

HRID 328531 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.O1CCOCC1.[C:17]1([NH:23][NH2:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.N1C=CC=CC=1>O>[C:17]1([N:23]([C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([I:1])=[CH:3][CH:4]=2)[NH2:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 7516PhenylhydrazineHCID 312751,4-DioxaneHCID 743734-Iodobenzoyl chloride

Product 1

HCID 54307176p-Iodobenzoic acid phenylhydrazideYield 70.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 44.7 g. (0.168 mole) of p-iodobenzoyl chloride in 100 ml. of dioxane was added to 18.2 g. (0.168 mole) of phenylhydrazine dissolved in 250 ml. of pyridine at 5° to 15° C,. The resulting suspension was stirred at about 25° C. for 3 days, poured into 2 liters of water, the solids were filtered and washed with water, dilute aqueous hydrochloric acid and then again with water. The product thus obtained was crystallized from ethanol to give 40.0 g. (70.9% yield) of p-iodobenzoic acid phenylhydrazide having a melting point of 210° to 211° C.

Workup

  1. customat 5° to 15° C
  2. filtrationthe solids were filtered
  3. washwashed with water, dilute aqueous hydrochloric acid
  4. customThe product thus obtained
  5. customwas crystallized from ethanol
  6. customto give 40.0 g

Sources & evidence

ORD record
ord-aaaaf97fbf654f3bb431d398f0647f99
Source dataset
uspto-grants-1977_04
Patent number
US04017540

Reaction notes

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