Sodium Hydroxide → Hydrazine, (3-bromo-4-chlorophenyl)-, hydrochloride (1:?)

HRID 66564Notes

Reaction equation

HRID 66564 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].[N:10]([O-])=O.[Na+].S(=O)(O)[O-].[Na+].[OH-].[Na+]>Cl.O>[ClH:9].[Br:1][C:2]1[CH:3]=[C:4]([NH:5][NH2:10])[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 128437223-Bromo-4-chloroanilineHCID 23665763Sodium BisulfiteHCID 23668193Sodium Nitrite

Product 1

HCID 20530451Hydrazine, (3-bromo-4-chlorophenyl)-, hydrochloride (1:?)

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
-10 °C

Procedure

3-Bromo-4-chloroaniline (41.3 g., 0.2 mole) in 90 ml of 6 N hydrochloric acid, cooled to -10° is treated with 14 g. of sodium nitrite in 30 ml. of water. Add this solution, with stirring, to a cold (-10° C.) solution of 55 g. of sodium bisulfite and 20 g. of sodium hydroxide in 200 ml. of water. After the red precipitate appears, allow the mixture to warm to room temperature. Add 200 ml. of concentrated hydrochloric acid and heat at 90°-100° C. for 4 hours. Allow the mixture to cool overnight, collect the material washing with 50 ml of cold 3 N hydrochloric acid. The product is dried. Recrystallization from ether-methanol yields the desired material, m.p. 208°-210° C.

Workup

  1. additionis treated with 14 g
  2. additionAdd this solution
  3. temperatureto warm to room temperature
  4. additionAdd 200 ml
  5. temperatureAllow the mixture to cool overnight
  6. customcollect the material
  7. washwashing with 50 ml of cold 3 N hydrochloric acid
  8. customThe product is dried
  9. customRecrystallization from ether-methanol

Sources & evidence

ORD record
ord-476aba35d4a44bc3b4a6d16998bdd945
Source dataset
uspto-grants-1982_08
Patent number
US04342769

Reaction notes

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