Acetic Acid → HCID 68548621, compound

HRID 2242177Notes

Reaction equation

HRID 2242177 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C:5]([C:10](=O)[C:11]1[CH:16]=[C:15](C)[CH:14]=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19])=[CH:6][N:7](C)C)[CH3:2].Cl.[CH2:24]([O:26][C:27](=[O:31])[CH2:28][NH:29]N)[CH3:25].[C:32](O)(=O)C>C(O)C>[CH2:1]([O:3][C:4]([C:5]1[CH:6]=[N:7][N:29]([CH2:28][C:27]([O:26][CH2:24][CH3:25])=[O:31])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([CH3:32])=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19])=[O:22])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11593468Acetic acid, 2-hydrazinyl-, ethyl ester, hydrochloride (1:1)HCID 68542455HCID 68542455, compound

Product 1

HCID 68548621HCID 68548621, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above crude 3-dimethylamino-2-(5-methyl-2-nitro-benzoyl)-acrylic acid ethyl ester j (3.06 g, 10 mmol) and the hydrazino-acetic acid ethyl ester hydro chloride (1.64 g, 10 mmol) were refluxed in absolute ethanol containing catalytic amount of acetic acid for 8 h. The reaction mixture was cooled and concentrated in vacuo. The residue was purified by column chromatography to provide pure compound 1 (1.81 g, 50% yield for two steps): LC MS (Method B): 362 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-a6112639e6d04be980af24c4948a3c38
Source dataset
uspto-grants-2010_03
Patent number
US07671069B2

Reaction notes

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