Allyl bromide → HCID 13109063, compound

HRID 1462971Notes

Reaction equation

HRID 1462971 reaction equation
[OH:1][C:2]1[C:13]2=[C:14]3[CH:9]([CH2:10][C:11]4[CH:18]=[C:17]([OH:19])[C:16]([O:20][CH3:21])=[CH:15][C:12]=42)[NH:8][CH2:7][CH2:6][C:5]3=[CH:4][C:3]=1[O:22][CH3:23].C(=O)(O)[O-].[Na+].[CH2:29](Br)[CH:30]=[CH2:31]>CN(C)C=O>[CH2:31]([N:8]1[CH:9]2[C:14]3=[C:13]([C:2]([OH:1])=[C:3]([O:22][CH3:23])[CH:4]=[C:5]3[CH2:6][CH2:7]1)[C:12]1[CH:15]=[C:16]([O:20][CH3:21])[C:17]([OH:19])=[CH:18][C:11]=1[CH2:10]2)[CH:30]=[CH2:29]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 516892Sodium BicarbonateHCID 1453991023599-69-1

Product 1

HCID 13109063HCID 13109063, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

582 mg. (1.85 mmol) (+)-5,6,6a,7-Tetrahydro-1,9-dihydroxy-2,10-dimethoxy-4H-dibenzo(de,g)quinoline are dissolved in 10 ml. dimethylformamide. After the addition of 385 mg. (4.58 mmol) sodium bicarbonate and 0.2 ml. (279.6 mg.; 2.31 mmol) allyl bromide, the reaction mixture is stirred for 30 minutes at ambient temperature and thereafter heated under reflux for 2 hours. Subsequently, the solvent is evaporated off in a vacuum and the residue is partitioned between chloroform and water. After working up and crystallising from chloroform/diethyl ether, there is obtained (+)-6-allyl-5,6,6a,7-tetrahydro-1,9-dihydroxy-2,10-dimethoxy-4H-dibenzo(de,g)quinoline; m.p. 161°-171° C.

Workup

  1. additionAfter the addition of 385 mg
  2. temperatureheated
  3. temperatureunder reflux for 2 hours
  4. customSubsequently, the solvent is evaporated off in a vacuum
  5. customthe residue is partitioned between chloroform and water
  6. customcrystallising from chloroform/diethyl ether

Sources & evidence

ORD record
ord-1de26b0939394995a538294a914c3ef4
Source dataset
uspto-grants-1984_07
Patent number
US04461895

Reaction notes

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