Hydrazine → 2,4-Dimethoxybenzohydrazide

HRID 10731

Reaction equation

HRID 10731 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[O:12][CH3:13].[NH2:15][NH2:16]>CO>[CH3:13][O:12][C:5]1[CH:6]=[C:7]([O:10][CH3:11])[CH:8]=[CH:9][C:4]=1[C:3]([NH:15][NH2:16])=[O:2]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 137451Benzoic acid, 2,4-dimethoxy-, methyl ester

Product 1

HCID 4567282,4-DimethoxybenzohydrazideYield 78.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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).

Workup

  1. customSolvent was removed under reduced pressure
  2. dissolutionThe residue was re-dissolved in ethyl acetate
  3. washThe solution of ethyl acetate was washed with saturated solution of sodium bicarbonate and brine
  4. dry with materialdried over sodium carbonate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-665a71c8df494a06987f1f3e49f3c7d1
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Linked notes

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