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

HRID 83789

反応式

HRID 83789 の反応式
[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=1>CN(C)C=O.[Ni]>[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1

参加物

4

反応物 1

HCID 146502956-(4-Nitrophenoxy)-hexanoic acid methyl ester

生成物 1

HCID 146502966-(4-Aminophenoxy)-hexanoic acid methyl ester収率 78.8%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  1. customCatalyst was removed by filtration and dimethyl formamide
  2. distillationdistilled off under vacuum
  3. customCrude 17 was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-68d8e3382d704997bd548e91ad074dec
出典データセット
uspto-grants-2014_09
特許番号
US08846845B2

関連ノート

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