Hydrazine hydrate (1:1) → Methyl 2-[4-(aminomethyl)phenyl]benzoate

HRID 1646922

반응식

HRID 1646922 반응식
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:28]=[CH:27][C:14]([CH2:15][N:16]2C(=O)C3=CC=CC=C3C2=O)=[CH:13][CH:12]=1)([O:3][CH3:4])=[O:2].O.NN>C(O)C>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:12]=[CH:13][C:14]([CH2:15][NH2:16])=[CH:27][CH:28]=1)([O:3][CH3:4])=[O:2]

참가 물질

4

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 19794415N-[4-(2-Carbomethoxyphenyl)benzyl]phthalimide

생성물 1

HCID 1393434Methyl 2-[4-(aminomethyl)phenyl]benzoate수율 66.3%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Compound (f) of Example 6 (3.85 g, 0.01 mole) is dissolved in 100 mL of absolute ethanol with warming. Hydrazine hydrate (7.5 mL) is added at once. The solution is heated to reflux for 10 minutes and the reaction mixture sets up. The mixture is cooled to room temperature and filtered. The precipitate is washed with excess hot ethanol. The ethanol fraction is rotovapped to a pale yellow oil. Chromatography on silica gel using methylene chloride/25% methanol as the mobile phase yields 1.6 g (66%) of a pale yellow oil. 1H NMR (CDCl3) 7.83 (1H, d, J=7 Hz); 7.6-7.2 (7H, m); 3.92 (2H, s); 3.66 (3H, s); 2.16 (2H, bs). Mass Spec. (DCI) m/z 242 (M+H). Analysis-calc'd for C15H15NO2.H2O: C, 71.97; H, 6.44; N, 5.60; found: C, 71.60; H, 6.27; N, 5.70.

후처리

  1. temperaturewith warming
  2. temperatureThe solution is heated
  3. temperatureto reflux for 10 minutes
  4. filtrationfiltered
  5. washThe precipitate is washed with excess hot ethanol

출처 및 근거

ORD 기록
ord-b05d08e10ace4944bcf7e1059762d3a6
출처 데이터셋
uspto-grants-1993_01
특허 번호
US05182288

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