Hydrazine hydrate (1:1) → 3-Methyl-2-phenylbutanehydrazide

HRID 388269Notes

Reaction equation

HRID 388269 reaction equation
[CH3:1][CH:2]([CH3:14])[CH:3]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:4](OC)=[O:5].O.[NH2:16][NH2:17]>>[CH3:1][CH:2]([CH3:14])[CH:3]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:4]([NH:16][NH2:17])=[O:5]

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 5051294Methyl 3-methyl-2-phenylbutanoate

Product 1

HCID 591858993-Methyl-2-phenylbutanehydrazideYield 47%

Procedure

A stirred solution of methyl 3-methyl-2-phenylbutanoate (0.87 g, 1 eq) and hydrazine hydrate (10 mL) was heated at 110° C. for 12 h. 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 (0.17 g, 47%) that was purified by column chromatography over silica gel to yield the product (0.61 g).

Workup

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

Sources & evidence

ORD record
ord-5f8a95886bd140b7b291494a4efa12d1
Source dataset
uspto-grants-2013_02
Patent number
US08377930B2

Reaction notes

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