Reaktion #10827

Reaktionsgleichung

hydrazine

2,4-dimethoxy-benzoic acid methyl ester

→

2,4-dimethoxy-benzoic acid hydrazide

Ausbeute 78.1%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeSolvent was removed under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was re-dissolved in ethyl acetate
3. 3
   WaschenThe solution of ethyl acetate was washed with saturated solution of sodium bicarbonate and brine
4. 4
   Trocknendried over sodium carbonate
5. 5
   Einengenconcentrated

Vorschrift

Ex-109A: A solution of 2,4-dimethoxy-benzoic acid methyl ester (4.24 g, 21.6 mmol) and hydrazine (3.4 mL, 108.1 mmol) in methanol (50 mL) was refluxed overnight. Solvent was removed under reduced pressure. The residue was re-dissolved in ethyl acetate. The solution of ethyl acetate was washed with saturated solution of sodium bicarbonate and brine, dried over sodium carbonate and concentrated to afford 2,4-dimethoxy-benzoic acid hydrazide (3.31 g, 78%) as a white solid: 1H NMR (CDCl3) δ 8.77 (bs, 1H), 8.15 (d, J=8.8 Hz, 1H), 6.58 (dd, J=8.8, 2.2 Hz, 1H), 6.46 (d, J=2.2 Hz, 1H), 4.10 (bs, 2H), 3.91 (s, 3H), 3.83 (s, 3H).

Quelle