Bromide ion → HCID 53881747, compound

HRID 1957541Notes

Reaction equation

HRID 1957541 reaction equation
[CH2:1]([C:4]1[C:13]([OH:14])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][C:8](=[O:24])[N:9]2[CH2:15][CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:2]=[CH2:3].[CH2:25]([C:28]1[CH:37]=[C:36]2[C:31](CCC(=O)N2CC=CC2C=CC=CC=2)=[CH:30][C:29]=1O)[CH:26]=[CH2:27].[Br-]>CO.[OH-].[K+]>[CH2:1]([C:4]1[C:13]([O:14][CH2:27][CH:26]=[CH:25][C:28]2[CH:37]=[CH:36][CH:31]=[CH:30][CH:29]=2)=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][C:8](=[O:24])[N:9]2[CH2:15][CH:16]=[CH:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 259Bromide ionHCID 53778809HCID 53778809, compoundHCID 54244883HCID 54244883, compound

Product 1

HCID 53881747HCID 53881747, compoundYield 41.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

3.19 Grams of the mixture of 5-allyl-1-cinnamyl-3,4-dihydro-6-hydroxy-2(1H)-quinolinone and 7-allyl-1-cinnamyl-3,4-dihydro-6-hydroxy-2(1H)-quinolinone obtained in Example 13 was dissolved in 100 ml of methanol containing 1 g of potassium hydroxide. Under stirring, 2 g of cinnamy bromide was added thereto at room temperature, then stirred at room temperature for 1 hour, further stirred at 60° C. for 4 hours. After the reaction was finished, the reaction mixture was concentrated to a half volume under reduced pressure, 100 ml of water was added and stirred vigorously, then extracted with 200 ml of ethyl acetate. The extract was washed with water and an aqueous solution saturated with sodium chloride and dried with anhydrous magnesium sulfate. The magnesium sulfate was removed by filtration, the filtrate was concentrated to dryness. The residue was subjected to treatment by means of a silica gel flush column chromatography by using a mixed solvent of ethyl acetate: n-hexane as the eluent. The second eluted portion was collected and concentrated and crystallized from diethyl ether-n-hexane, there was obtained 1.8 g (41.4%) of 5-allyl-1-cinnamyl-6-cinnamyloxy-3,4-dihydro-2(1H)-quinolinone. Colorless granular crystals (recrystallized from diethyl ether-n-hexane). Melting point: 66°-68° C.

Workup

  1. stirringat room temperature, then stirred at room temperature for 1 hour
  2. stirringfurther stirred at 60° C. for 4 hours
  3. concentrationthe reaction mixture was concentrated to a half volume under reduced pressure, 100 ml of water
  4. additionwas added
  5. stirringstirred vigorously
  6. extractionextracted with 200 ml of ethyl acetate
  7. washThe extract was washed with water
  8. dry with materialan aqueous solution saturated with sodium chloride and dried with anhydrous magnesium sulfate
  9. customThe magnesium sulfate was removed by filtration
  10. concentrationthe filtrate was concentrated to dryness
  11. customflush column chromatography
  12. customThe second eluted portion was collected
  13. concentrationconcentrated
  14. customcrystallized from diethyl ether-n-hexane

Sources & evidence

ORD record
ord-4e3aa08a047f407cb3a5a1a1ccccea40
Source dataset
uspto-grants-1998_07
Patent number
US05786367

Reaction notes

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