Acetic Acid → HCID 58428266, compound

HRID 1408306Notes

Reaction equation

HRID 1408306 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=O)[CH2:13][C:14]([C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=2)=O)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].O.[NH2:28][NH2:29].C(O)(=O)C>C(O)C>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]([C:16]3[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=3)[NH:29][N:28]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 58428320HCID 58428320, compound

Product 1

HCID 58428266HCID 58428266, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

190 mg (0.54 mmol) methyl 4-[3-(4-butoxyphenyl)-3-oxopropanoyl]benzoate was dissolved in 10 mL ethanol and 0.5 mL hydrazine hydrate and 1 mL acetic acid were added. The mixture was refluxed for 1 h. Upon cooling, the product crystallized. To complete crystallisation, 5 mL water was added and the product was filtered off, washed with water and dried. A white crystalline material (150 mg, 0.42 mmol, 78%) was isolated and directly used for the next step.

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. temperatureUpon cooling
  3. customthe product crystallized
  4. customTo complete crystallisation, 5 mL water
  5. additionwas added
  6. filtrationthe product was filtered off
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-2133aca5e2a94c239f84b7dbf2c7ac2d
Source dataset
uspto-grants-2014_12
Patent number
US08921309B2

Reaction notes

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