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

HRID 909105ノート

反応式

HRID 909105 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.O.[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

5

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 3

HCID 935Nickel触媒HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

A mixture of 4-cyano-2-methoxy-benzoic acid methyl ester (1.01 g, 5.28 mmol) in methanol (50 mL) was added to Raney-nickel 2800 slurry in water (a few grams washed with methanol to remove the water, Aldrich) and it was put under a 50 psi hydrogen atmosphere for 16 hrs. The mixture was filtered through Celite under an argon atmosphere and concentrated and then purified by flash chromatography to give 4-aminomethyl-2-methoxy-benzoic acid methyl ester (385.7 mg, 34.7%).

後処理

  1. washwashed with methanol
  2. customto remove the water, Aldrich) and it
  3. filtrationThe mixture was filtered through Celite under an argon atmosphere
  4. concentrationconcentrated
  5. custompurified by flash chromatography

出典と根拠

ORDレコード
ord-4a6147c96f02477a9904aa5a14830e57
出典データセット
uspto-grants-2011_09
特許番号
US08017607B2

反応ノート

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