Hydrochloric Acid → HCID 59331084, compound

HRID 2195594Notes

Reaction equation

HRID 2195594 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([C:16](=[O:18])[CH3:17])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[C:7]([C:19](=[O:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:26])[CH:8]=2)[CH3:2].[C:28](OCC)(=[O:30])[CH3:29].CC(C)([O-])C.[K+].Cl>O>[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([C:16](=[O:18])[CH2:17][C:28](=[O:30])[CH3:29])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[C:7]([C:19](=[O:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:26])[CH:8]=2)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 57481225HCID 57481225, compound

Product 1

HCID 59331084HCID 59331084, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A one liter four-necked flask equipped with a stirrer, a nitrogen inlet tube, a reflex condenser, and a thermometer was charged with 35.54 g of 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone, 264.33 g of ethyl acetate, and 33.66 g of potassium t-butoxide, and the mixture was refluxed in a nitrogen atmosphere for 5 hours. After cooling to room temperature, 100 ml of ion exchanged water and 100 ml of 6N hydrochloric acid were successively added, followed by stirring. The organic phase was separated and washed with a sodium chloride aqueous solution until neutral. A hundred fifty milliliters of n-hexane was added thereto, followed by cooling with ice for crystallization. The solid precipitated was collected by filtration by suction and dried under reduced pressure to give 17.29 g (43%) of pale yellow crystals, which had a melting point of 148° C. and was identified by various analyses to be β-diketone compound No. 3 having a carbazolyl group.

Workup

  1. customA one liter 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. washwashed with a sodium chloride aqueous solution until neutral
  6. additionA hundred fifty milliliters of n-hexane was added
  7. temperatureby cooling with ice for crystallization
  8. customThe solid precipitated
  9. filtrationwas collected by filtration by suction
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-dbb079e6a4154ce99d09028d6c3e4765
Source dataset
uspto-grants-2012_12
Patent number
US08338081B2

Reaction notes

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