Hydrazine hydrate (1:1) → 3-Methoxy-4-nitrobenzohydrazide

HRID 419334

Reaction equation

HRID 419334 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:6](OC)=[O:7].O.[NH2:17][NH2:18]>CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:6]([NH:17][NH2:18])=[O:7]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 287308Methyl 3-methoxy-4-nitrobenzoate

Product 1

HCID 218838753-Methoxy-4-nitrobenzohydrazideYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To methyl 3-methoxy-4-nitrobenzoate (5.16 g, 24.5 mmol) in EtOH (250 mL) was added hydrazine monohydrate (5.95 mL, 122 mmol) in one portion. The reaction was heated at 80° C. overnight and concentrated upon completion by TLC. The residue was taken up in EtOAc, heated and hot filtered. The filtrate was concentrated and the residue was triturated with diethyl ether to provide the title compound (3.65 g, 17.3 mmol, 71%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.96 (s, 3H), 4.60 (br. s., 2H), 7.50 (dd, J=8.4, 1.5 Hz, 1H), 7.69 (d, J=1.8 Hz, 1H), 7.93 (d, J=8.1 Hz, 1H), 10.05 (br. s., 1H).

Workup

  1. concentrationconcentrated upon completion by TLC
  2. temperatureheated
  3. concentrationThe filtrate was concentrated
  4. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-8caec853cd82465a9d01bdaf8f8adf24
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Linked notes

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