3-Chloro-4-methoxyaniline → (3-Chloro-4-methoxyphenyl)hydrazine--hydrogen chloride (1/1)

HRID 429316Notes

Reaction equation

HRID 429316 reaction equation
[N:1]([O-])=O.[Na+].[Cl:5][C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[NH2:9]>O.Cl>[ClH:5].[Cl:5][C:6]1[CH:7]=[C:8]([NH:9][NH2:1])[CH:10]=[CH:11][C:12]=1[O:13][CH3:14]

Participants

5

Reactant 2

HCID 214413-Chloro-4-methoxyanilineHCID 23668193Sodium Nitrite

Product 1

HCID 16495456(3-Chloro-4-methoxyphenyl)hydrazine--hydrogen chloride (1/1)Yield 173.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Procedure

A solution of sodium nitrite (6 g) in water (50 ml) was added dropwise to a solution of 3-chloro-4-methoxyaniline (10 g) in concentrated hydrochloric acid (30 ml) at 0° C. with stirring. After the addition was completed, the reaction mixture was stirred at the same temperature for 1 hour. A solution of stannous chloride dihydrate (50 g) in concentrated hydrochloric acid (30 ml) was added dropwise at 0° C. The resulting mixture was stirred for 2 hours at the same temperature. The resulting precipitate was collected by filtration, washed with ice water and dried in vacuo at 50° C. to afford (3-chloro-4-methoxyphenyl)hydrazine hydrochloride (11.5 g) as a yellow brown solid.

Workup

  1. additionAfter the addition
  2. stirringthe reaction mixture was stirred at the same temperature for 1 hour
  3. stirringThe resulting mixture was stirred for 2 hours at the same temperature
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with ice water
  6. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-f5cd6e83e0fe4815a4fc7f91dfbc66b6
Source dataset
uspto-grants-2001_11
Patent number
US06316485B1

Reaction notes

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