Sulfuric Acid → 1-(4-Nitrophenyl)cyclobutanecarbonitrile
Reaction equation
[C:1]1([C:7]2([C:11]#[N:12])[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OS(O)(=O)=O.[N+:18]([O-])([O-:20])=[O:19].[K+]>C(O)(=O)C>[N+:18]([C:4]1[CH:5]=[CH:6][C:1]([C:7]2([C:11]#[N:12])[CH2:10][CH2:9][CH2:8]2)=[CH:2][CH:3]=1)([O-:20])=[O:19]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A mixture of 1-phenylcyclobutanecarbonitrile (5 g) and acetic acid (15 ml) and H2SO4 (10 ml) and KNO3 (1.1 eq) was stirred at 0° C. for 20 min. The mixture was warmed to RT and stirred for two hours. The mixture was poured on ice and stirred until all ice melted. The precipitate was filtered and recrystalized from EtOH to give 1-(4-nitrophenyl)-cyclobutanecarbonitrile. The above product (2 g) was mixed with Pd—C (10%, 800 mg) in EtOH (100 ml) and hydrogenated under H2 atmosphere for 1 hour. The reaction was filtered through Celite and evaporated to give 1-(4-aminophenyl)-cyclobutanecarbonitrile, Mass: (M+1) 172, which was used for next step without further purification.
Workup
- temperatureThe mixture was warmed to RT
- stirringstirred for two hours
- additionThe mixture was poured on ice
- stirringstirred until all ice
- filtrationThe precipitate was filtered
- customrecrystalized from EtOH
Sources & evidence
- ORD record
- ord-6a4c74ce069d4885af84e6f812794803
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07129252B2
Reaction notes
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