Sodium Hydroxide → HCID 20379950, compound

HRID 2072389Notes

Reaction equation

HRID 2072389 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([NH:9][C:10]([C:12]3=[CH:13][CH:14]=[CH:15][C:3](=[C:4]23)[CH:2]=1)=[O:11])=[O:8].[OH-].[Na+].Br[CH:19]1[CH2:23][CH2:22][O:21][C:20]1=[O:24].[Na].O=C1C(N2CC3C=CC=C4C=3C(=CC=C4)C2)CCO1>CN(C)C=O.C(O)C>[O:24]=[C:20]1[CH:19]([N:9]2[C:10](=[O:11])[C:12]3[CH:13]=[CH:14][CH:15]=[C:3]4[C:4]=3[C:5](=[CH:6][CH:1]=[CH:2]4)[C:7]2=[O:8])[CH2:23][CH2:22][O:21]1

Participants

8

Reactant 5

HCID 14798Sodium HydroxideHCID 66491NaphthalimideHCID 954632(3H)-Furanone, 3-bromodihydro-HCID 5360545SodiumHCID 86735103HCID 86735103, compound

Product 1

HCID 20379950HCID 20379950, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent2×

Procedure

10 g. (0.0507 moles) of naphthalimide is dissolved in 200 ml. of hot (90°) dimethylformamide with stirring. 2.06 g. (0.0507 moles) of sodium hydroxide dissolved in 50 ml. of hot ethanol is added causing the naphthalimide sodium salt to precipitate. The sodium salt is filtered off at room temperature, washed with ethanol, and is taken up in 200 ml. of hot (90 °) dimethylformamide. 8.37 g. (0.0507 moles) of 3-bromo-4,5-dihydro-2(3H)-furanone in a small amount of dimethylformamide is added to the sodium salt solution. This mixture is heated at from 80° to 100° for an hour and crude organic material is precipitated by the addition of 500 ml. of water. This material is filtered off, washed with water and recrystallized from 600 ml. of dioxane. Additional recrystallization from 25 ml. of dimethylformamide/25 ml. of isopropyl alcohol yields 3.1 g. of 2-(tetrahydro-2-oxo-3-furanyl)-1H-benz[de]isoquinoline-1,3(2H-dione; m.p. 310°-312°.

Workup

  1. customto precipitate
  2. filtrationThe sodium salt is filtered off at room temperature
  3. washwashed with ethanol
  4. customof hot (90 °) dimethylformamide
  5. temperatureThis mixture is heated at from 80° to 100° for an hour
  6. customcrude organic material is precipitated by the addition of 500 ml
  7. filtrationThis material is filtered off
  8. washwashed with water
  9. customrecrystallized from 600 ml
  10. customAdditional recrystallization from 25 ml
  11. customof isopropyl alcohol yields 3.1 g

Sources & evidence

ORD record
ord-d67f9bb5c42b4a5980a30486dcef028c
Source dataset
uspto-grants-1977_09
Patent number
US04051246

Reaction notes

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