Hydrazine hydrate (1:1) → 2,2-Diphenylacetohydrazide

HRID 388258Notes

Reaction equation

HRID 388258 reaction equation
[C:1]1([CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8](OC)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[NH2:19][NH2:20]>CCO>[C:1]1([CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([NH:19][NH2:20])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 77019Methyl alpha-phenylbenzeneacetate

Product 1

HCID 2261392,2-DiphenylacetohydrazideYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of methyl 2,2-diphenylacetate (0.5 g, 1 equiv) in anhydrous EtOH (150 mL) was added hydrazine hydrate (8 mL) and heated to reflux. Stirring was then continued for 1 hour. The reaction mixture was then cooled and the solvents removed under reduced pressure. The crude oil was diluted with EtOAc and washed with H2O and the organic phase dried over Na2SO4, filtered, and the solvents removed under reduced pressure to yield a yellow oil (0.97 g, 97%) that was used without further purification.

Workup

  1. temperatureheated to reflux
  2. temperatureThe reaction mixture was then cooled
  3. customthe solvents removed under reduced pressure
  4. additionThe crude oil was diluted with EtOAc
  5. washwashed with H2O
  6. dry with materialthe organic phase dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvents removed under reduced pressure

Sources & evidence

ORD record
ord-245f2a0a060f4062b6cc4b5c7f07d2ec
Source dataset
uspto-grants-2013_02
Patent number
US08377930B2

Reaction notes

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