HCID 19035269, compound → HCID 19035262, compound

HRID 263821Notes

Reaction equation

HRID 263821 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[C:8]([O:14][CH2:15][CH3:16])=[CH:7][C:6]=1[CH3:17]>CO.[Pd]>[NH2:11][C:9]1[C:8]([O:14][CH2:15][CH3:16])=[CH:7][C:6]([CH3:17])=[C:5]([NH:4][CH2:3][CH2:2][OH:1])[CH:10]=1

Participants

4

Reactant 1

HCID 19035269HCID 19035269, compound

Product 1

HCID 19035262HCID 19035262, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

644 mg (2.7 mmol) of 2-(2'-hydroxyethyl)amino-5-ethoxy-4-nitrotoluene were hydrogenated with a catalytic amount of palladium/active carbon (5% Pd) in 50 ml methanol. After filtering off the catalyst, the solvent was completely distilled away. 428 mg (76% of theoretical yield) of 4-amino-2-(2'-hydroxyethyl)amino-5-ethoxytoluene were obtained in pure form by thin layer chromatography. The obtained product crystals melted at 128° C.

Workup

  1. filtrationAfter filtering off the catalyst
  2. distillationthe solvent was completely distilled away

Sources & evidence

ORD record
ord-4d1bb10175a54ec2a9a890be5db899a3
Source dataset
uspto-grants-1997_07
Patent number
US05645610

Reaction notes

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