3,5-Heptanedione → HCID 58256810, compound

HRID 1013049Notes

Reaction equation

HRID 1013049 reaction equation
[CH3:1][CH2:2][C:3](=O)[CH2:4][C:5](=O)[CH2:6][CH3:7].Cl.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][NH2:20])=[CH:15][CH:14]=1>C(O)C>[CH2:2]([C:3]1[CH:4]=[C:5]([CH2:6][CH3:7])[N:19]([C:16]2[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)[N:20]=1)[CH3:1]

Participants

4

Reactant 2

HCID 819233,5-HeptanedioneHCID 27239044-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 58256810HCID 58256810, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3,5-heptanedione (1.06 mL, 7.80 mmol) and 4-methoxyphenylhydrazine hydrochloride (1.49 g, 8.58 mmol) in ethanol (25 mL) was stirred at 60° C. overnight. After the reaction was concentrated, the residue was partitioned between 1 N HCl and ethyl acetate. The ethyl acetate layer was washed two times with 1 N HCl. The organic layer was dried (MgSO4) and concentrated to give 893 mg of the title compound. LC-MS (C14H18N2O calculated 230) m/z 231 (M+H).

Workup

  1. concentrationAfter the reaction was concentrated
  2. customthe residue was partitioned between 1 N HCl and ethyl acetate
  3. washThe ethyl acetate layer was washed two times with 1 N HCl
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3209c571dbdc4f8bb5c2c796cd05ea84
Source dataset
uspto-grants-2011_07
Patent number
US07981896B2

Reaction notes

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