Propargyl bromide → HCID 14851948, compound

HRID 1032772Notes

Reaction equation

HRID 1032772 reaction equation
[CH3:1][C:2](C)([O-])[CH3:3].[K+].[NH:7]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]3[CH2:16][CH2:17][CH2:18][CH:9]([C:10]=23)[C:8]1=[O:19].C(Br)C#C>CN(C)C=O.O>[CH2:3]([C:9]12[CH2:18][CH2:17][CH2:16][C:11]3[C:10]1=[C:15]([CH:14]=[CH:13][CH:12]=3)[NH:7][C:8]2=[O:19])[C:2]#[CH:1]

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 5993752a,3,4,5-Tetrahydrobenzo[cd]indol-2(1H)-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 14851948HCID 14851948, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium tert.-butoxide, 4.94 g (0.044 mol), was added to a solution of 6.92 g (0.04 mol) of rac-2a,3,4,5-tetrahydro-benz[cd]indol-2(1H)-one in 50 ml of dimethylformamide. After stirring for 15 minutes under nitrogen, 5.23 g or 3.9 ml of propargyl bromide was added and stirring was continued for 30 minutes. The mixture was diluted with water and ice and the precipitate was collected by filtration, washed with water and sucked dry. The solids were dissolved in methylene chloride and the solution was dried and evaporated. Crystallization of the residue from ethyl acetate gave crude product of rac-2a,3,4,5-tetrahydro-2a-(2-propynyl)benz[cd]indol-2(1H)-one with m.p. 174-177° which was recrystallized from ethyl acetate to melt at 177°-180°.

Workup

  1. stirringstirring
  2. waitwas continued for 30 minutes
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with water
  5. customsucked dry
  6. dissolutionThe solids were dissolved in methylene chloride
  7. customthe solution was dried
  8. customevaporated
  9. customCrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-2973ae4fd7bc4f38823903fda57858c8
Source dataset
uspto-grants-1990_09
Patent number
US04959361

Reaction notes

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