Reaction #10827

Reaction equation

hydrazine

2,4-dimethoxy-benzoic acid methyl ester

→

2,4-dimethoxy-benzoic acid hydrazide

Yield 78.1%

Solvents

methanol

Conditions

Workup

1. 1
   OtherSolvent was removed under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was re-dissolved in ethyl acetate
3. 3
   WashThe solution of ethyl acetate was washed with saturated solution of sodium bicarbonate and brine
4. 4
   Dryingdried over sodium carbonate
5. 5
   Concentrationconcentrated

Procedure

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).

Source