Acetic Acid → HCID 14851939, compound

HRID 1032752Notes

Reaction equation

HRID 1032752 reaction equation
[CH3:1][C:2](C)([O-])[CH3:3].[K+].[CH:7]1[CH:12]=[C:11]2[C:13]([NH:15][C:16]([C:18]3=[CH:19][CH:20]=[CH:21][C:9](=[C:10]23)[CH:8]=1)=[O:17])=[O:14].C(Br)C#C.C(O)(=O)C>CN(C)C=O>[CH2:3]([N:15]1[C:16](=[O:17])[C:18]2[CH:19]=[CH:20][CH:21]=[C:9]3[C:10]=2[C:11](=[CH:12][CH:7]=[CH:8]3)[C:13]1=[O:14])[C:2]#[CH:1]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7842Propargyl bromideHCID 66491NaphthalimideHCID 23665647Potassium tert-butoxide

Product 1

HCID 14851939HCID 14851939, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-20 °C

Procedure

Potassium t-butoxide, 6.2 g (0.055 mol) was added to a solution of 9.9 g (0.05 mol) of naphthalimide in 50 ml of dimethylformamide cooled to -20° C. After stirring in the cold for 1 hour, 5 ml (0.055 mol) of propargyl bromide in 20 ml of dimethylformamide was added and the mixture was allowed to warm to room temperature. It was then heated to 45° C. for 45 minutes. After cooling, 15 ml of glacial acetic acid was added and the product was precipitated by addition of water. The solids were collected and recrystallized from ethyl acetate to leave 10 g (84%) of colorless crystals of 2-(2-propynyl)-1H-benz[de]isoquinoline-1,3-(2H)-dione with m.p. 235°-237° C.

Workup

  1. temperatureto warm to room temperature
  2. temperatureIt was then heated to 45° C. for 45 minutes
  3. temperatureAfter cooling
  4. customthe product was precipitated by addition of water
  5. customThe solids were collected
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-97f842226a6c43f8b299ce9ee19e9870
Source dataset
uspto-grants-1990_09
Patent number
US04959361

Reaction notes

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