trans-N-Octyl-2-(4-nitrophenyl)cyclopropanecarboxamide → trans-N-octyl-2-(4-aminophenyl)cyclopropanecarboxamide
Reaction equation
[CH2:1]([NH:9][C:10]([C@@H:12]1[CH2:14][C@H:13]1[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=1)=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]>[Fe].C(O)(=O)C>[CH2:1]([NH:9][C:10]([C@@H:12]1[CH2:14][C@H:13]1[C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1)=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred solution of 6.2 g. of trans-N-octyl-2-(4-nitrophenyl)cyclopropanecarboxamide in 70 ml. of glacial acetic acid, at 85° C., was added 5.3 g. of iron powder, portionwise, during 10 minutes. The temperature was kept between 85° and 90° C. during the addition. At the end of the addition, stirring was continued at 85°-90° C. for 10 minutes, and then the hot reaction mixture was filtered. The filtrate was evaporated in vacuo, and the residue thus obtained was partitioned between 350 ml. of ethyl acetate and 150 ml. of saturated sodium chloride solution. The ethyl acetate layer was removed, dried using sodium sulfate, and evaporated in vacuo. This gave 5.4 g. of the title compound as a yellow solid.
Workup
- additionThe temperature was kept between 85° and 90° C. during the addition
- additionAt the end of the addition
- filtrationthe hot reaction mixture was filtered
- customThe filtrate was evaporated in vacuo
- customthe residue thus obtained
- customwas partitioned between 350 ml
- customThe ethyl acetate layer was removed
- customdried
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-2094a272cb414ea3839746e0bbc318a5
- Source dataset
- uspto-grants-1982_05
- Patent number
- US04331683
Reaction notes
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