4-Isopropoxyaniline → HCID 53420788, compound
Reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)[CH3:3].[N:12]([O-])=O.[Na+].[Cl:16][Sn]Cl.O>Cl.O>[ClH:16].[CH:2]([O:4][C:5]1[CH:11]=[CH:10][C:8]([NH:9][NH2:12])=[CH:7][CH:6]=1)([CH3:1])[CH3:3]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 2.5 °C
Procedure
To a stirred solution of 4-(propan-2-yloxy)aniline (5.0 g, 33.07 mmol, 1.00 equiv) in 2N hydrochloric acid (35 mL) at 0° C. was added dropwise a solution of sodium nitrite (2.4 g, 34.78 mmol, 1.05 equiv) in water (8 mL). The reaction mixture was stirred at 0-5° C. for 1 h. A solution of SnCl2.H2O (15 g, 66.37 mmol, 2.01 equiv) in 12N hydrochloric acid (20 mL) was then added dropwise at 0-5° C. The resulting mixture was stirred at room temperature overnight. The precipitates was collected by filtration to give 4.7 g (70%) of crude (4-isopropoxyphenyl)hydrazine hydrochloride as a purple solid. The product was used in the next step without further purification.
Workup
- stirringThe resulting mixture was stirred at room temperature overnight
- filtrationThe precipitates was collected by filtration
Sources & evidence
- ORD record
- ord-254d14dcb3fa467c88a852fb45717ae4
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365527B2
Reaction notes
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