Stannous chloride dihydrate → (2,4-Dichloro-5-(1-methylethoxy)phenyl)hydrazine
Reaction equation
[N:1]([O-])=O.[Na+].[Cl:5][C:6]1[CH:12]=[C:11]([Cl:13])[C:10]([O:14][CH:15]([CH3:17])[CH3:16])=[CH:9][C:7]=1[NH2:8].O.O.[Sn](Cl)Cl>O.Cl>[Cl:5][C:6]1[CH:12]=[C:11]([Cl:13])[C:10]([O:14][CH:15]([CH3:17])[CH3:16])=[CH:9][C:7]=1[NH:8][NH2:1]Participants
Conditions
- Temperature
- 0 °C
Procedure
A solution of 15.8 g (0.23 mole) of sodium nitrite in 100 mL of water was added to a stirred solution of 50.0 g (0.23 mole) of 2,4-dichloro-5-(1-methylethoxy)aniline in 250 mL of concentrated hydrochloric acid at 0° C. over 30 minutes. After complete addition, the mixture was stirred at 0° C. for 30 minutes. A solution of 114.0 g (0.506 mole) of tin (II) chloride dihydrate in 125 mL of concentrated hydrochloric acid was added dropwise to the reaction mixture. After complete addition, the mixture was stirred for one hour. The resultant white slurry was filtered. The filter cake was added to a 20% aqueous sodium hydroxide solution and stirred for 30 minutes. The basic mixture was filtered, and the filter cake recrystallized from methanol and water to yield 37.0 g of 2,4-dichloro-5-(1-methylethoxy)phenylhydrazine.
Workup
- additionAfter complete addition
- additionAfter complete addition
- stirringthe mixture was stirred for one hour
- filtrationThe resultant white slurry was filtered
- additionThe filter cake was added to a 20% aqueous sodium hydroxide solution
- stirringstirred for 30 minutes
- filtrationThe basic mixture was filtered
- customthe filter cake recrystallized from methanol and water
Sources & evidence
- ORD record
- ord-78bf53a94b124c428a5765caa7d8360e
- Source dataset
- uspto-grants-1988_08
- Patent number
- US04766233
Reaction notes
Loading…