p-Toluenesulfonic acid monohydrate → Methyl 4-cyano-2-methoxybenzoate

HRID 1807260ノート

反応式

HRID 1807260 の反応式
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([O:12][CH3:13])[CH:4]=1)#[N:2].O.[C:15]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:15][O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[CH:4][C:5]=1[O:12][CH3:13]

参加物

4

反応物 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 151660044-Cyano-2-methoxybenzoic acid

生成物 1

HCID 57426183Methyl 4-cyano-2-methoxybenzoate収率 367.8%

試薬・触媒・溶媒 1

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. temperatureheated
  2. temperatureto reflux for 16 hrs
  3. customThe solvent was removed
  4. extractionthe reaction residue was extracted with EtOAc
  5. washwashed with saturated sodium carbonate, water, and saturated NaCl
  6. dry with materialdried over Na2SO4

出典と根拠

ORDレコード
ord-584a2a7083af4124b3742acbab614677
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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