Phenylhydrazine → HCID 20542766, compound

HRID 2285969Notes

Reaction equation

HRID 2285969 reaction equation
[C:1]([CH2:7][C:8](=O)[CH2:9][CH:10]([CH3:12])[CH3:11])(=O)[CH2:2][CH:3]([CH3:5])[CH3:4].[H-].[Na+].C([O:18][C:19](=[O:22])[CH2:20]Br)C.[C:23]1([NH:29][NH2:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)(=O)C.C1C=CC=CC=1>[CH2:2]([C:1]1[C:7]([CH2:20][C:19]([OH:18])=[O:22])=[C:8]([CH2:9][CH:10]([CH3:12])[CH3:11])[N:29]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:30]=1)[CH:3]([CH3:5])[CH3:4]

Participants

7

Reactant 4

HCID 7516PhenylhydrazineHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 581379DIISOVALERYLMETHANE

Product 1

HCID 20542766HCID 20542766, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 241BenzeneSolvent

Procedure

10 grams diisovalerylmethane (as described by Swamer and Hauser), were reacted with 1.3 gram of a 50% suspension of sodium hydride in paraffin oil and 10 grams bromoacetic acid-ethylester by a procedure analogous to that described in Example (2b). The benzene solution obtained in this procedure was evaporated and the residue of crude 3,3-diisovalerylpropionic acid-ethyl ester obtained thereby was mixed with 6.5 grams phenylhydrazine and 4 grams glacial acetic acid and the mixture was heated to the boiling temperature under reflux for 2 hours. The reaction mixture obtained thereby was then worked up in accordance with a procedure analogous to that described in Example (1a). The ester thus recovered was saponified and the free acid recovered by a procedure analogous to that described in Example (1b). 7.5 grams 3,5-diisobutyl-1-phenyl-pyrazol-4-acetic acid, melting at 125°-126° C., were obtained representing a yield of 44% on the diisovalerylmethane starting material.

Workup

  1. customwas evaporated
  2. customthe residue of crude 3,3-diisovalerylpropionic acid-ethyl ester obtained
  3. temperaturethe mixture was heated to the boiling temperature
  4. temperatureunder reflux for 2 hours
  5. customThe reaction mixture obtained
  6. customThe ester thus recovered
  7. customthe free acid recovered by a procedure analogous to

Sources & evidence

ORD record
ord-1a7d8813803d4d13a8a301ae558ab689
Source dataset
uspto-grants-1982_04
Patent number
US04325962

Reaction notes

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