Triethylamine → 3-Ethoxy-4-nitrobenzohydrazide

HRID 523097Notes

Reaction equation

HRID 523097 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:7](O)=[O:8])[CH3:2].C(N(CC)CC)C.ClC(OCC)=O.O.[NH2:30][NH2:31]>C1COCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:7]([NH:30][NH2:31])=[O:8])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 24654Hydrazine hydrate (1:1)HCID 223975093-Ethoxy-4-nitrobenzoic acid

Product 1

HCID 899955863-Ethoxy-4-nitrobenzohydrazideYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Ethoxy-4-nitrobenzoic acid (PCT Int Appl. 2008003958, 1.06 g 5.02 mmole) was stirred with dry THF (10 mL) and triethylamine (0.86 mL, 6.1 mmol) and the solution was cooled in an ice bath. Ethyl chloroformate (0.56 mL, 5.85 mmol) was added dropwise and the reaction was stirred in the ice bath for 15 minutes. Hydrazine hydrate (1.27 mL, 26 mmol) was added in one portion and the reaction stirred in the ice bath for 5 minutes and then at 20° C. for 1 hour. The reaction was concentrated in vacuo, partitioned between EtOAc (100 mL) and saturated aqueous sodium bicarbonate (15 mL). The organic layer was collected, washed with brine, dried over sodium sulfate and concentrated in vacuo to afford the title compound (1.07 g, 95%).

Workup

  1. temperaturethe solution was cooled in an ice bath
  2. concentrationThe reaction was concentrated in vacuo
  3. custompartitioned between EtOAc (100 mL) and saturated aqueous sodium bicarbonate (15 mL)
  4. customThe organic layer was collected
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a4140a088ac8450b99941c6cdce08882
Source dataset
uspto-grants-2016_05
Patent number
US09334286B2

Reaction notes

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