Sodium hydride → HCID 19067990, compound

HRID 1957540Notes

Reaction equation

HRID 1957540 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH2:15][CH:16]=[CH2:17])[NH:10][C:9](=[O:18])[CH2:8][CH2:7]2)[CH:2]=[CH2:3].[H-].[Na+].[CH2:21](Br)[CH:22]=[C:23]([CH3:25])[CH3:24]>CN(C)C=O>[CH2:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH2:15][CH:16]=[CH2:17])[N:10]([CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])[C:9](=[O:18])[CH2:8][CH2:7]2)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 700922-Butene, 1-bromo-3-methyl-HCID 19067969HCID 19067969, compound

Product 1

HCID 19067990HCID 19067990, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

81 Grams of 6-allyl-7-allyloxy-3,4-dihydro-2(1H)-quinolinone obtained in Example 15 was dissolved in 500 ml of dimethylformamide, then 13 g of 60% oily sodium hydride and 50 g of prenyl bromide were added thereto and reacted similarly as in Example 17, after the reaction was finished, the reaction mixture was treated similarly, there was obtained yellow oily product. This oily product was subjected to treatment by means of a silica gel flush column chromatography by using a mixed solvent of methylene chloride-methanol (100:1) as the eluent. The secondary eluted portion was collected and concentrated, there was obtained 67 g (64.6%) of 6-allyl-7-allyloxy-3,4-dihydro-1-prenyl-2(1H)-quinolinone as pale yellow oily product. This oily product become a solid matter then it was allowed to stand at below 20° C., the solid matter was washed with ice-cooled petroleum ether to change white solid, dried in a desiccator and pulverized, there was isolated white powdery product.

Workup

  1. customreacted similarly as in Example 17
  2. additionthe reaction mixture was treated similarly
  3. customthere was obtained yellow oily product
  4. customflush column chromatography
  5. customThe secondary eluted portion was collected
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1ba69391e4dd44e4b1f723d9c81d6b8c
Source dataset
uspto-grants-1998_07
Patent number
US05786367

Reaction notes

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