Propargyl bromide → HCID 13109066, compound

HRID 1462981Notes

Reaction equation

HRID 1462981 reaction equation
[OH:1][C:2]1[C:13]2=[C:14]3[CH:9]([CH2:10][C:11]4[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[CH:15][C:12]=42)[NH:8][CH2:7][CH2:6][C:5]3=[CH:4][C:3]=1[O:23][CH3:24].C(=O)(O)[O-].[Na+].[CH2:30](Br)[C:31]#[CH:32]>C(O)C>[CH2:32]([N:8]1[CH:9]2[C:14]3=[C:13]([C:2]([OH:1])=[C:3]([O:23][CH3:24])[CH:4]=[C:5]3[CH2:6][CH2:7]1)[C:12]1[CH:15]=[C:16]([O:21][CH3:22])[C:17]([O:19][CH3:20])=[CH:18][C:11]=1[CH2:10]2)[C:31]#[CH:30]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 516892Sodium BicarbonateHCID 12444945HCID 12444945, compound

Product 1

HCID 13109066HCID 13109066, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

12.0 g. (2.7 mmol) (±)-5,6,6a,7-Tetrahydro-1-hydroxy-2,9,10-trimethoxy-4H-dibenzo(de,g)quinoline are dissolved in 25 ml. ethanol and mixed with 560 mg. sodium bicarbonate and 0.26 ml. (2.95 mmol) propargyl bromide. The reaction mixture is stirred for 1 hour at ambient temperature and then for 2 hours at 80° C. under reflux. The usual working up and crystallisation from ethanol gives (±)-6-propargyl-5,6,6a,7-tetrahydro-1-hydroxy-2,9,10-trimethoxy-4H-dibenzo(de,g)quinoline;

Workup

  1. temperaturefor 2 hours at 80° C. under reflux
  2. customcrystallisation from ethanol

Sources & evidence

ORD record
ord-8f70b505cd50410980a0eba14af7d919
Source dataset
uspto-grants-1984_07
Patent number
US04461895

Reaction notes

Loading…