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

HRID 1807261노트

반응식

HRID 1807261 반응식
[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]

참가 물질

4

반응물 1

HCID 57426183Methyl 4-cyano-2-methoxybenzoate

생성물 1

HCID 67094960Methyl 4-(aminomethyl)-2-methoxybenzoate수율 37.4%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 887Methanol용매

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-1091679f84ff45c5b24764c2a9390693
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354444B2

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