Methylhydrazine → HCID 18408509, compound

HRID 993008Notes

Reaction equation

HRID 993008 reaction equation
O[C:2]([C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=1)=[CH:3][C:4](=O)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:23][NH:24][NH2:25]>C(O)C>[CH3:23][N:24]1[C:2]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=2)=[CH:3][C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N:25]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 67524928HCID 67524928, compound

Product 1

HCID 18408509HCID 18408509, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 4-hydroxy-2-oxo-4-(3,4,5-trimethoxyphenyl)-3-butenoate (3.0 g) was dissolved in ethanol (30 mL), and to the solution methylhydrazine (468 mg) was added, and the mixture was stirred at 80° C. for 2 hours. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate, washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was then purified by column chromatography on silica gel (hexane:ethyl acetate=2:1) to obtain the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was then purified by column chromatography on silica gel (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-a613514ffc924f8b8f28c622c73a63f6
Source dataset
uspto-grants-2002_10
Patent number
US06472386B1

Reaction notes

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