Hydrazine hydrate (1:1) → 3-Nitro-5-trifluoromethyl-benzoic acid hydrazide

HRID 1050117Notes

Reaction equation

HRID 1050117 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=1)[C:7](OC)=[O:8])([O-:3])=[O:2].O.[NH2:19][NH2:20]>CO>[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=1)[C:7]([NH:19][NH2:20])=[O:8])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 18942157Methyl 3-nitro-5-(trifluoromethyl)benzoate

Product 1

HCID 716286233-Nitro-5-trifluoromethyl-benzoic acid hydrazideYield 90.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of methyl 3-nitro-5-(trifluoromethyl)benzoate (20 g, 80 mmol) and hydrazine hydrate (5.56 mL, 96 mmol) in MeOH (100 mL) was stirred for 16 h at 25° C. Then the solvent was concentrated to yield an off white solid of 3-nitro-5-(trifluoromethyl)benzohydrazide (20 g, 72.2 mmol, 90% yield): 1H NMR (400 MHz, CD3OD) δ 8.89 (s, 1H), 8.65 (s, 1H), 8.50 (s, 1H); ES-LCMS m/z 250 (M+H).

Workup

  1. concentrationThen the solvent was concentrated

Sources & evidence

ORD record
ord-40ece5250f174212b10236e01392dead
Source dataset
uspto-grants-2016_07
Patent number
US09382238B2

Reaction notes

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