Methyl 4-cyano-2-methoxybenzoate → Methyl 4-(aminomethyl)-2-methoxybenzoate

HRID 1807261ノート

反応式

HRID 1807261 の反応式
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][C:5]=1[O:12][CH3:13]>CO.[Ni]>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH2:11])=[CH:6][C:5]=1[O:12][CH3:13]

参加物

4

反応物 1

HCID 57426183Methyl 4-cyano-2-methoxybenzoate

生成物 1

HCID 67094960Methyl 4-(aminomethyl)-2-methoxybenzoate収率 37.4%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 887Methanol溶媒

実験手順

A solution of 4-cyano-2-methoxy benzoic acid (1.0 g, 5.65 mmol, Biogene) in methanol was reacted with p-toluenesulfonic acid monohydrate (285.6 mg, 1.479 mmol) and heated to reflux for 16 hrs. The solvent was removed and the reaction residue was extracted with EtOAc, and washed with saturated sodium carbonate, water, and saturated NaCl, and dried over Na2SO4 to give 4-Cyano-2-methoxy-benzoic acid methyl ester (1.04 g, 96%). This ester (1.01 g, 5.28 mmol) in methanol (50 mL) was reacted with Raney Ni (3 spatula tips full, exact amount unknown, Aldrich) under 50 psi H2 in a Parr apparatus for 16 hrs. After filtering through Celite and concentrating, the crude mixture was purified by silica gel chromatography using methanol and methylene chloride to give 4-aminomethyl-2-methoxy-benzoic acid methyl ester (385.7 mg, 37%).

後処理

  1. filtrationAfter filtering through Celite
  2. concentrationconcentrating
  3. customthe crude mixture was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-1091679f84ff45c5b24764c2a9390693
出典データセット
uspto-grants-2013_01
特許番号
US08354444B2

反応ノート

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