Phenylhydrazine → HCID 178499532, compound

HRID 1520725Notes

Reaction equation

HRID 1520725 reaction equation
O=[C:2]([CH2:8][C:9]([O:11]C)=O)[CH2:3][C:4]([O:6][CH3:7])=[O:5].[C:13]1([NH:19][NH2:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1C=CC=CC=1>[OH:11][C:9]1[N:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:20]=[C:2]([CH2:3][C:4]([O:6][CH3:7])=[O:5])[CH:8]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 74591Dimethyl 3-oxoglutarate

Product 1

HCID 178499532HCID 178499532, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The mixture of dimethyl 3-oxopentanedioate (10 mmol, 1.74 g) and phenylhydrazine (10 mmol, 1.08 g) in dry benzene (50 ml) was refluxed for 8 h, then solvent was removed in vacuo and the title compound was separated by recrystallization from i-PrOH (20 ml). Yield: 80%. 1HNMR (500 MHz, DMSO-d6, ppm): 3.49 (2H, s), 3.68 (3H, s), 5.43 (1H, s), 7.12 (1H, t, 7.4 Hz), 7.35 (2H, t, 7.6 Hz), 7.78 (2H, d, 7.9 Hz), 11.1 (1H, bs)

Workup

  1. temperaturewas refluxed for 8 h
  2. customsolvent was removed in vacuo
  3. customthe title compound was separated by recrystallization from i-PrOH (20 ml)

Sources & evidence

ORD record
ord-52e2bc34ce384d488118cc3db5c434aa
Source dataset
uspto-grants-2015_07
Patent number
US09073919B2

Reaction notes

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