Acetic Acid → 1-(2-propynyl)benz[cd]indol-2(1H)-one

HRID 1032753Notes

Reaction equation

HRID 1032753 reaction equation
[CH3:1][C:2](C)([O-])[CH3:3].[K+].[NH:7]1[C:15]2[C:10]3[C:11](=[CH:16][CH:17]=[CH:18][C:9]=3[C:8]1=[O:19])[CH:12]=[CH:13][CH:14]=2.C(Br)C#C.C(O)(=O)C>CN(C)C=O>[CH2:3]([N:7]1[C:15]2[C:10]3[C:11](=[CH:16][CH:17]=[CH:18][C:9]=3[C:8]1=[O:19])[CH:12]=[CH:13][CH:14]=2)[C:2]#[CH:1]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7842Propargyl bromideHCID 67222benz(cd)indol-2(1H)-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 148519401-(2-propynyl)benz[cd]indol-2(1H)-oneYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium-t-butoxide, 6.17 g (0.055 mol) was added to a solution of 8.46 g (5 mmol) of benz[cd]indol-2(1H)-one in 100 ml of dimethylformamide. After stirring for 10 minutes at room temperature, 4.9 ml (0.055 mol) of propargyl bromide was added and the mixture was stirred for 1 hour at room temperature. The reaction mixture was acidified with acetic acid and partitioned between methylene chloride and saturated aqueous sodium bicarbonate solution. The organic layer was dried and evaporated and the residue was crystallized from tetrahydrofuran/ethanol to leave 8 g (77%) of product with m.p. 183°-186° C. The title compound was recrystallized for analysis twice from methylene chloride/ethyl acetate and had m.p. 185°-187° C.

Workup

  1. stirringthe mixture was stirred for 1 hour at room temperature
  2. custompartitioned between methylene chloride and saturated aqueous sodium bicarbonate solution
  3. customThe organic layer was dried
  4. customevaporated
  5. customthe residue was crystallized from tetrahydrofuran/ethanol

Sources & evidence

ORD record
ord-2efaf01b5b1c418198ebe1f7f645803f
Source dataset
uspto-grants-1990_09
Patent number
US04959361

Reaction notes

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