Hydrochloric Acid → 3-Cyano-4-methoxyphenylhydrazine

HRID 850062Notes

Reaction equation

HRID 850062 reaction equation
[N:1]([O-])=O.[Na+].Cl.Cl.[C:7]([C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[NH2:12])#[N:8]>>[C:7]([C:9]1[CH:10]=[C:11]([NH:12][NH2:1])[CH:13]=[CH:14][C:15]=1[O:16][CH3:17])#[N:8]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 193660253-Cyano-4-methoxyaniline hydrochlorideHCID 23668193Sodium Nitrite

Product 1

HCID 183553923-Cyano-4-methoxyphenylhydrazineYield 69.1%

Procedure

To an aqueous solution (150 ml) of 3-cyano-4-methoxyaniline hydrochloride (72 g) were added sodium nitrite (29.7 g), stannous chloride dihydrate (266 g) and con. hydrochloric acid (437 ml) with stirring under ice-cooling. After the completion of the reaction, precipitated crystals were collected by filtration. The crystals were added to water, and the mixture was neutralized with aqueous sodium hydroxide solution, extracted with a mixed solvent of toluene and tert-butanol, washed with water and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give 44 g of 3-cyano-4-methoxyphenylhydrazine.

Workup

  1. temperaturecooling
  2. customAfter the completion of the reaction
  3. customprecipitated crystals
  4. filtrationwere collected by filtration
  5. additionThe crystals were added to water
  6. extractionextracted with a mixed solvent of toluene and tert-butanol
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-2e4e40ca7397454dac86a44f3feb1571
Source dataset
uspto-grants-2000_01
Patent number
US06015829

Reaction notes

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