Hydrazine hydrate (1:1) → 3-Nitrobenzohydrazide

HRID 1747192Notes

Reaction equation

HRID 1747192 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7](OC)=[O:8])([O-:3])=[O:2].O.[NH2:15][NH2:16]>CCO>[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([NH:15][NH2:16])=[O:8])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 69260Methyl 3-nitrobenzoate

Product 1

HCID 32914983-Nitrobenzohydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 3-nitrobenzoate (940.70 mg; 5.19 mmol; 1.00 eq.) is dissolved in EtOH (24.00 ml). Hydrazine hydrate (4.04 ml; 83.09 mmol; 16.00 eq.) is added and the mixture is stirred 1 hour at RT. It is stirred at 60° C. for 6 hours and RT overnight. The precipitate formed is filtrated and dried under vacuo, affording 3-nitrobenzohydrazide as white-off solid (815.90 mg; 86.73%). 1H NMR (DMSO-d6) δ: 4.62 (s, 2H), 7.76 (m, 1H), 8.24 (m, 1H), 8.36 (m, 1H), 8.63 (s, 1H), 10.15 (s, 1H).

Workup

  1. stirringIt is stirred at 60° C. for 6 hours and RT overnight
  2. customThe precipitate formed
  3. filtrationis filtrated
  4. customdried under vacuo

Sources & evidence

ORD record
ord-229332175cb24edaa33bfb8c2da0c0d5
Source dataset
uspto-grants-2015_10
Patent number
US09150561B2

Reaction notes

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