HCID 19366026, compound → HCID 19366030, compound

HRID 850064Notes

Reaction equation

HRID 850064 reaction equation
Cl.[C:2]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])[NH2:7])#[N:3].[N:17]([O-])=O.[Na+]>>[C:2]([C:4]1[CH:5]=[C:6]([NH:7][NH2:17])[CH:8]=[CH:9][C:10]=1[O:11][CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])#[N:3]

Participants

3

Reactant 2

HCID 19366026HCID 19366026, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 19366030HCID 19366030, compoundYield 88.9%

Procedure

To an aqueous solution (33 ml) of 3-cyano-4-neopentyloxyaniline hydrochloride (21 g) were added sodium nitrite (6.7 g), stannous chloride dihydrate (59.5 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 17 g of 3-cyano-4-neopentyloxy-phenylhydrazine.

Workup

  1. additionhydrochloric add (100 ml)
  2. temperaturecooling
  3. customAfter the completion of the reaction
  4. customprecipitated crystals
  5. filtrationwere collected by filtration The crystals
  6. additionwere 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-1fd900b5a74e44ea950e62aef5028c9e
Source dataset
uspto-grants-2000_01
Patent number
US06015829

Reaction notes

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