Hydrazine → HCID 90020746, compound

HRID 2200137Notes

Reaction equation

HRID 2200137 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-])=O.[NH2:18][NH2:19]>C(O)C>[NH2:1][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:18][NH2:19])=[O:8]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 18942157Methyl 3-nitro-5-(trifluoromethyl)benzoate

Product 1

HCID 90020746HCID 90020746, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Mix methyl 3-nitro-5-(trifluoromethyl)benzoate (1.8 g, 12 mmol), ethanol (6 mL) and 80% (w/w) hydrazine (10 mL), reflux overnight. Concentrate the mixture, partition the resulting residue between ethyl acetate and water, collect the organic layer, wash with sodium bicarbonate, dry over anhydrous sodium sulfate, and concentrate under reduced pressure to give the crude product (1.23 g, 77%) which is used in next step without further purification.

Workup

  1. temperaturereflux overnight
  2. concentrationConcentrate the mixture
  3. custompartition the resulting residue between ethyl acetate and water
  4. customcollect the organic layer
  5. washwash with sodium bicarbonate
  6. dry with materialdry over anhydrous sodium sulfate
  7. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-d87c7ebc9e174c0f87ca650ac45121ec
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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