Reacción #10827

Ecuación de reacción

hydrazine

2,4-dimethoxy-benzoic acid methyl ester

→

2,4-dimethoxy-benzoic acid hydrazide

Rendimiento 78.1%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroSolvent was removed under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was re-dissolved in ethyl acetate
3. 3
   LavadoThe solution of ethyl acetate was washed with saturated solution of sodium bicarbonate and brine
4. 4
   Secadodried over sodium carbonate
5. 5
   Concentraciónconcentrated

Procedimiento

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).

Fuente