2-Naphthalenesulfonic acid → methoxy-N-(2-methoxy-1-methylethyl)-3,4-Xylidine

HRID 1703529Notes

Reaction equation

HRID 1703529 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=O)=[CH:7][C:3]=1[CH2:4]OC.[CH3:14][O:15][CH2:16][C:17](=O)[CH3:18].[CH:20]1C2C(=CC=CC=2)C=CC=1S(O)(=O)=O>[Pt]>[CH3:20][O:13][N:11]([CH:17]([CH3:18])[CH2:16][O:15][CH3:14])[C:8]1[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([CH3:4])[CH:7]=1

Participants

5

Reactant 3

HCID 84202-Naphthalenesulfonic acidHCID 22172MethoxyacetoneHCID 12767666Methyl 2-methyl-5-nitrobenzyl ether

Product 1

HCID 20563862methoxy-N-(2-methoxy-1-methylethyl)-3,4-Xylidine

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

Procedure

A mixture of methyl 2-methyl-5-nitrobenzyl ether (12 g, 0.066M), methoxyacetone [20 g (used as solvent)], 2-naphthalenesulfonic acid (0.3 g) and 5% Pt/C (0.7 g) is shaken on a Parr hydrogenator maintaining the temperature below 40° with external cooling. The theoretical amount of hydrogen (0.26M) is consumed and further uptake ceases after 2 hours.

Workup

  1. temperaturemaintaining the temperature below 40° with external cooling
  2. customThe theoretical amount of hydrogen (0.26M) is consumed

Sources & evidence

ORD record
ord-7e854d4f22c9421fbe43520b06696dff
Source dataset
uspto-grants-1978_11
Patent number
US04124639

Reaction notes

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