Sodium hydride → HCID 53943986, compound

HRID 1957543Notes

Reaction equation

HRID 1957543 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14]CC=C)[NH:10][C:9](=[O:18])[CH2:8][CH2:7]2)[CH:2]=[CH2:3].[CH2:19]([C:22]1[C:23](OCC=C)=[CH:24][CH:25]=[C:26]2[C:31]=1NC(=O)CC2)[CH:20]=[CH2:21].[H-].[Na+].[CH2:39](Br)[CH:40]=[CH:41]C1C=CC=CC=1>CN(C)C=O.C1C2C(=CC=CC=2)CCC1>[CH2:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([CH2:41][CH:40]=[CH2:39])[C:13]=1[OH:14])[N:10]([CH2:21][CH:20]=[CH:19][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:31]=1)[C:9](=[O:18])[CH2:8][CH2:7]2)[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 98116BromomethylstyreneHCID 19067969HCID 19067969, compound2×HCID 19068025HCID 19068025, compound

Product 1

HCID 53943986HCID 53943986, compoundYield 33.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8404TetralinSolvent

Procedure

2.4 Grams of the mixture of 6-allyl-7-allyloxy-3,4-dihydro-2(1H)-quinolinone and 6-allyl-7-allyloxy-3,4-dihydro-2(1H)-quinolinone as the reaction intermediate obtained in Example 14 was dissolved in 20 ml of dimethylformamide, then 0.6 g of 60% oily sodium hydride and 2.5 g of cinnamyl bromide were added thereto at room temperature and reacted similarly as in Reference example 7, there was obtained yellow oily product by treating thus obtained reaction mixture. Said oily product was dissolved in 50 ml of tetralin and stirred at 200° to 230° C. for 3 hours. After cooling, the reaction mixture was subjected to purification by passing through a silica gel column, there was obtained 1.2 g (33.4%) of 6,8-diallyl-1-cinnamyl-3,4-dihydro-7-hydroxy-2(1H)-quinolinone. Pale yellow flake crystals (recrystallized from isopropyl ether). Melting point: 132°-138° C.

Workup

  1. customat room temperature and reacted similarly as in Reference example 7
  2. customthere was obtained yellow oily product
  3. additionby treating thus obtained
  4. customreaction mixture
  5. temperatureAfter cooling
  6. customthe reaction mixture was subjected to purification

Sources & evidence

ORD record
ord-ff8ac662e6e8438a998862aac1438556
Source dataset
uspto-grants-1998_07
Patent number
US05786367

Reaction notes

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