3-Cyano-4-isobutoxyaniline hydrochloride → 3-Cyano-4-isobutoxy-phenylhydrazine

HRID 850063Notes

Reaction equation

HRID 850063 reaction equation
Cl.[C:2]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH:13]([CH3:15])[CH3:14])[NH2:7])#[N:3].[N:16]([O-])=O.[Na+]>>[C:2]([C:4]1[CH:5]=[C:6]([NH:7][NH2:16])[CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH:13]([CH3:15])[CH3:14])#[N:3]

Participants

3

Reactant 2

HCID 193660273-Cyano-4-isobutoxyaniline hydrochlorideHCID 23668193Sodium Nitrite

Product 1

HCID 154065483-Cyano-4-isobutoxy-phenylhydrazineYield 82.8%

Procedure

To an aqueous solution (34 ml) of 3-cyano-4-isobutoxyaniline hydrochloride (20 g) were added sodium nitrite (6.8 g), stannous chloride dihydrate (61 g) and con. hydrochloric add (100 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 15 g of 3-cyano-4-isobutoxy-phenylhydrazine.

Workup

  1. additionhydrochloric add (100 ml)
  2. temperaturecooling
  3. customAfter the completion of the reaction
  4. customprecipitated crystals
  5. filtrationwere collected by filtration
  6. additionThe crystals were added to water
  7. extractionextracted with a mixed solvent of toluene and tert-butanol
  8. washwashed with water
  9. dry with materialdried over magnesium sulfate
  10. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7930b7ff2d62446faaf6dfcd2c408bfc
Source dataset
uspto-grants-2000_01
Patent number
US06015829

Reaction notes

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