2-(Chloromethyl)-1-ethyl-4-nitrobenzene → 4-Ethyl-3-methylaniline
Reaction equation
Cl[CH2:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[CH2:12][CH3:13].[H][H]>C(O)(=O)C.[Pd]>[CH2:12]([C:4]1[CH:5]=[CH:6][C:7]([NH2:9])=[CH:8][C:3]=1[CH3:2])[CH3:13]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
α-Chloro-2-ethyl-5-nitrotoluene (40.0 g.) was dissolved in glacial acetic acid and shaken with 5% Pd/C in a hydrogen atmosphere (6.7 g.) in a Parr hydrogenator. When reduction was complete, the crude product was isolated, taken up in ether, washed with water, dilute base and water. After stirring the ether solution over solid K2CO3, the product was isolated as a liquid, 96% pure by glc.
Sources & evidence
- ORD record
- ord-4d0ff86dcd1b402c95de2138df8f2bae
- Source dataset
- uspto-grants-1978_11
- Patent number
- US04124639
Reaction notes
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