3-(tert-Butyl)aniline hydrochloride → (3-Tert-butylphenyl)hydrazine

HRID 1589670Notes

Reaction equation

HRID 1589670 reaction equation
Cl.[C:2]([C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][CH:12]=1)[NH2:9])([CH3:5])([CH3:4])[CH3:3].[N:13]([O-])=O.[Na+]>Cl.O>[C:2]([C:6]1[CH:7]=[C:8]([NH:9][NH2:13])[CH:10]=[CH:11][CH:12]=1)([CH3:5])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 202458563-(tert-Butyl)aniline hydrochlorideHCID 23668193Sodium Nitrite

Product 1

HCID 2735691(3-Tert-butylphenyl)hydrazine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

3-t-Butylaniline hydrochloride (5 g) in concentrated hydrochloric acid (8 ml) was stirred at 0° whilst a solution of sodium nitrite (1.86 g) in water (2.4 ml) was slowly added. The mixture was kept at 0° for 1 hour and, after filtering (at 0°), it was treated dropwise with a solution of stannous chloride dihydrate (18.2 g) in concentrated hydrochloric acid (18.8 ml). A pink-coloured solid separated. After 1 hour, this solid was filtered off and washed with saturated aqueous sodium chloride. The resulting salt was converted into base in the usual way to give 3-t-butylphenylhydrazine, b.p. 88°-90°/0.25 mm Hg.

Workup

  1. additionwas slowly added
  2. filtrationafter filtering (at 0°), it
  3. additionwas treated dropwise with a solution of stannous chloride dihydrate (18.2 g) in concentrated hydrochloric acid (18.8 ml)
  4. customA pink-coloured solid separated
  5. waitAfter 1 hour
  6. filtrationthis solid was filtered off
  7. washwashed with saturated aqueous sodium chloride

Sources & evidence

ORD record
ord-bfc20920b40e443989027765233210fa
Source dataset
uspto-grants-1986_02
Patent number
US04572913

Reaction notes

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