Benzoic Acid → HCID 20589204, compound

HRID 1111879Notes

Reaction equation

HRID 1111879 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH3:11])[C:7]([CH3:10])=[CH:8][CH:9]=1)([O-])=O.[CH2:12]([C:14](CC)=O)[CH3:13].[C:18](O)(=O)[C:19]1C=CC=CC=1.[H][H]>[Pd]>[CH2:18]([N:1]([CH2:13][CH2:12][CH3:14])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([CH3:11])[CH:5]=1)[CH3:19]

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 7288Ethyl ketoneHCID 74404-Nitro-o-xyleneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 20589204HCID 20589204, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

4-Nitro-o-xylene (10.0 g., 0.066 mole) is shaken in a Parr hydrogenator with diethyl ketone (20 ml., 0.019 mole), 5% palladium on carbon catalyst (0.5 g.) and benzoic acid (0.5 g.) with approximately 3 atmospheres of hydrogen. When the uptake of hydrogen is complete, the suspension is filtered and analyzed by gas-liquid chromatography demonstrating thereby that N-(1-ethyl)propyl-3,4-xylidine had been produced in 83% yield.

Workup

  1. filtrationthe suspension is filtered

Sources & evidence

ORD record
ord-99d537e2b34d45038980b0e2dfa1b324
Source dataset
uspto-grants-1978_10
Patent number
US04119669

Reaction notes

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