Reaction #170971

Reaction equation

6-(4-Nitrophenoxy)-hexanoic acid methyl ester

→

17

Yield 78.8%

6-(4-Aminophenoxy)-hexanoic acid methyl ester

Yield 78.8%

Solvents

dimethyl formamide

Conditions

Workup

1. 1
   OtherCatalyst was removed by filtration and dimethyl formamide
2. 2
   workup.DISTILLATIONdistilled off under vacuum
3. 3
   OtherCrude 17 was purified by column chromatography on silica gel

Procedure

Method-A Through a mixture of 6-(4-aminophenoxy)-hexanoic acid hydrochloride 16 (150 g, 578 mmol) in methanol (3 L) was passed dry HCl gas at 10° C. for 1 hour and refluxed for 48 hours. Methanol (1.5 L) was distilled off, ice water (1 L) was added and the pH adjusted to 7.5 with K2CO3. Crude 17 was extracted into chloroform, washed with 5% NaHCO3 solution, then water, and then dried over Na2SO4 and distilled to give 17 (60 g, 43.8%) as a thick brown syrup. Method-B 6-(4-Nitrophenoxy)-hexanoic acid methyl ester 21 (40 g, 149.81 mmol) was dissolved in dimethyl formamide (200 ml) in a pressure vessel. Raney nickel (20 g) was added and the mixture stirred under an atmosphere of hydrogen (4 kg) for 16 hours. Catalyst was removed by filtration and dimethyl formamide distilled off under vacuum. Crude 17 was purified by column chromatography on silica gel using chloroform as eluant to get pure 17 (28 grams, 78.8%) as a thick brown syrup.

Source