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

HRID 5862

反応式

HRID 5862 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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. (DCl) 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.

後処理

  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

出典と根拠

ORDレコード
ord-baca5479f4474cdbbe8a3aa3b0b1e8f4
出典データセット
uspto-grants-1993_09
特許番号
US05246940

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