2-(Chloromethyl)-1-ethyl-4-nitrobenzene → 4-Ethyl-3-methylaniline

HRID 1703531Notes

Reaction equation

HRID 1703531 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

HCID 123759392-(Chloromethyl)-1-ethyl-4-nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 148331384-Ethyl-3-methylaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

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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