Hydrochloric Acid → HCID 59331095, compound

HRID 2195592Notes

Reaction equation

HRID 2195592 reaction equation
[CH2:1]([N:4]1[C:16]2[CH:15]=[CH:14][C:13]([C:17](=[O:19])[CH3:18])=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:2][CH3:3].[C:20](OCC)(=[O:22])[CH3:21].CC(C)([O-])C.[K+].Cl>O>[CH2:1]([N:4]1[C:16]2[CH:15]=[CH:14][C:13]([C:17](=[O:19])[CH2:18][C:20](=[O:22])[CH3:21])=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 1912076HCID 1912076, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 59331095HCID 59331095, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 200 ml four-necked flask equipped with a stirrer, a nitrogen inlet tube, a reflex condenser, and a thermometer was charged with 25.13 g of 1-(9-propyl-9H-carbazol-3-yl)ethanone, 88.11 g of ethyl acetate, and 16.83 g of potassium t-butoxide, and the mixture was refluxed in a nitrogen atmosphere for 5 hours. After cooling to room temperature, 50 ml of ion exchanged water and 50 ml of 6N hydrochloric acid were successively added, followed by stirring. The organic phase was separated and mixed with 200 ml of ethyl acetate, and the mixture was washed with a sodium chloride aqueous solution until neutral. The upper layer was dried with magnesium sulfate, and the solvent was removed by evaporation. The solid thus precipitated was dissolved in 10 ml of ethyl acetate under reflux, and n-hexane was added thereto. The precipitate thus formed was collected by filtration and dried under reduced pressure to give 23.15 g (79%) of yellow crystals, which had a melting point of 97° C. and was identified by various analyses to be β-diketone compound No. 1 having a carbazolyl group.

Workup

  1. customA 200 ml four-necked flask equipped with a stirrer, a nitrogen inlet tube, a reflex condenser
  2. temperaturethe mixture was refluxed in a nitrogen atmosphere for 5 hours
  3. additionwere successively added
  4. customThe organic phase was separated
  5. additionmixed with 200 ml of ethyl acetate
  6. washthe mixture was washed with a sodium chloride aqueous solution until neutral
  7. dry with materialThe upper layer was dried with magnesium sulfate
  8. customthe solvent was removed by evaporation
  9. customThe solid thus precipitated
  10. dissolutionwas dissolved in 10 ml of ethyl acetate
  11. temperatureunder reflux
  12. additionn-hexane was added
  13. customThe precipitate thus formed
  14. filtrationwas collected by filtration
  15. customdried under reduced pressure

Sources & evidence

ORD record
ord-d79a239126ff4f98be8d63f533c2d2cf
Source dataset
uspto-grants-2012_12
Patent number
US08338081B2

Reaction notes

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