Acrylic Acid → HCID 54296403, compound

HRID 1900709Notes

Reaction equation

HRID 1900709 reaction equation
[NH2:1][C:2]1[CH2:7][CH:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:5][C:4](=[O:14])[CH:3]=1.[C:15](O)(=[O:18])[CH:16]=[CH2:17]>C(Cl)(Cl)Cl>[CH2:8]([CH:6]1[CH2:7][C:2]2[NH:1][C:15](=[O:18])[CH2:16][CH2:17][C:3]=2[C:4](=[O:14])[CH2:5]1)[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 6581Acrylic AcidHCID 54246996HCID 54246996, compound

Product 1

HCID 54296403HCID 54296403, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
140 °C

Procedure

The obtained 3-amino-5-n-hexyl-2-cyclohexene-1-one (16.8 g) and acrylic acid (12.4 g) were mixed, and the mixture was stirred at 140° C. for 2 hours. After completion of the reaction, chloroform was added, and the mixture was washed with sodium bicarbonate water, water and aqueous NaCl solution in this order, followed by drying over sodium sulfate. A crude product was obtained when the solvent was evaporated. The crude was purified by silica gel column chromatography (eluent=chloroform:methanol (50:1)). as a result, 11.2 g of 7-n-hexyl-1,2,3,4,5,6,7,8-octahydroquinoline-2,5-dione was obtained as colorless needles having a melting point of 142°-144° C. (52.0%).

Workup

  1. additionwas added
  2. washthe mixture was washed with sodium bicarbonate water, water and aqueous NaCl solution in this order
  3. dry with materialby drying over sodium sulfate
  4. customA crude product was obtained when the solvent
  5. customwas evaporated
  6. customThe crude was purified by silica gel column chromatography (eluent=chloroform:methanol (50:1))

Sources & evidence

ORD record
ord-2145a942e7f54c7e978762b5771c39cd
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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