Water → 3-(3-Cyclopentyloxy-4-methoxyanilino)-2-cyclopenten-1-one

HRID 1977596Notes

Reaction equation

HRID 1977596 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:11]=[CH:12][C:13]=2[O:14][CH3:15])[NH2:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:16]1(=O)[CH2:20][CH2:19][C:18](=[O:21])[CH2:17]1.O>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:11]=[CH:12][C:13]=2[O:14][CH3:15])[NH:10][C:16]2[CH2:20][CH2:19][C:18](=[O:21])[CH:17]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 962WaterHCID 774661,3-CyclopentanedioneHCID 27793343-(Cyclopentyloxy)-4-methoxyaniline

Product 1

HCID 155213543-(3-Cyclopentyloxy-4-methoxyanilino)-2-cyclopenten-1-oneYield 80.4%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

1.04 g (5.02 mole) of 3-cyclopentyloxy-4-methoxyaniline, 0.51 g (5.02 mmole) of 1,3-cyclopentanedione, and 0.03 g of p-toluenesulfonic acid were dissolved in 30 ml of benzene and the solution was heated reflux in an apparatus fitted with a water separation tube for 3 hours, while azeotropically separating the water produced. After the reaction, the solution was cooled to room temperature, a yellow crystal was precipitated. The precipitated yellow crystal was collected by suction filtration, and the crystal was washed with diethyl ether, then dried to obtain the title compound 1.16 g (yield 80.4%) as a pale yellow crystal.

Workup

  1. temperaturethe solution was heated
  2. temperaturereflux in an apparatus
  3. customwhile azeotropically separating the water
  4. customproduced
  5. customAfter the reaction
  6. customa yellow crystal was precipitated
  7. filtrationThe precipitated yellow crystal was collected by suction filtration
  8. washthe crystal was washed with diethyl ether
  9. customdried

Sources & evidence

ORD record
ord-9cf2ff8ce2414c7ea18ac18225e6876c
Source dataset
uspto-grants-2001_05
Patent number
US06235736B1

Reaction notes

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