Acetic acid, 2-hydrazinyl-, ethyl ester, hydrochloride (1:1) → HCID 59655957, compound

HRID 2054580Notes

Reaction equation

HRID 2054580 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.Cl.[NH:20]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[NH2:21]>C(O)C>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][N:20]1[CH:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[CH2:9][C:10]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)=[N:21]1)[CH3:27]

Participants

4

Reactant 2

HCID 11593468Acetic acid, 2-hydrazinyl-, ethyl ester, hydrochloride (1:1)HCID 69325438HCID 69325438, compound

Product 1

HCID 59655957HCID 59655957, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ([1-(4-bromophenyl)-3-(4-methoxypheyl)-propene]) (3.17 g, 10 mmol) and ethyl hydrazinoacetate hydrochloride (1.54 g, 10 mmol) in ethanol (50 mL) was heated to reflux for 4 h. After cooling to room temperature, the solution was concentrated, diluted with water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried over MgSO4, filtered and concentrated. Purification by flash column chromatography (5-10% ethyl acetate in heptane) provided [5-(4-bromo-phenyl)-3-(4-methoxy-phenyl)-4,5-dihydro-pyrazol-1-yl]-acetic acid ethyl ester (3.25 g, 78%) as an oil.

Workup

  1. temperatureto reflux for 4 h
  2. concentrationthe solution was concentrated
  3. additiondiluted with water (50 mL)
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash column chromatography (5-10% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-1f98ae2154e544c7a5896273c85ce442
Source dataset
uspto-grants-2008_02
Patent number
US07329680B2

Reaction notes

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