Acetic Acid → 1,4-Diketo-2,5-diethyl-3,6-bis(1-naphthyl)pyrrolo[3,4-c]pyrrole

HRID 393127

Reaction equation

HRID 393127 reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].[C:7]1([C:17]#[N:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1.[C:19]([O:29]C(C)C)(=O)[CH2:20][CH2:21][C:22]([O:24]C(C)C)=O.CI.[C:35](O)(=O)[CH3:36]>C(O)(CC)(C)C.CN(C=O)C.O.CO>[O:24]=[C:22]1[C:21]2=[C:1]([C:2]3[C:5]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[CH:9]=[CH:8][CH:3]=3)[N:18]([CH2:17][CH3:7])[C:19](=[O:29])[C:20]2=[C:17]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9][CH:8]=2)[N:18]1[CH2:35][CH3:36]

Participants

10

Reactant 5

HCID 176Acetic AcidHCID 6328Methyl iodideHCID 68461-NaphthalenecarbonitrileHCID 70213Diisopropyl succinateHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 226485811,4-Diketo-2,5-diethyl-3,6-bis(1-naphthyl)pyrrolo[3,4-c]pyrrole

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 64052-Methyl-2-butanolSolvent

Conditions

Temperature
90 °C

Procedure

In 36 mL of t-amyl alcohol, 7.3 g of potassium-t-butoxide were solved, and then 10 g of 1-naphthonitrile were added stirring the solution at 90° C. Into the solution, 6.7 mL of diisopropyl succinate were dropped taking time for 2 hours and were placed under reflux for one day. Next, 30 mL of methanol and 4.4 mL of acetic acid were added at 60° C. and then refluxed for 30 minutes. After cooling, the product was separated out through a filter and subsequently rinsed with methanol, thus resulting in a red powder. Next, 2.89 g of the resulting red powder were dissolved in 80 mL of DMF, and 2.1 g of potassium-t-butoxide were added and stirred for one hour. Then, 1.5 mL of methyl iodide was added and stirred at 65° C. for one day. After 50 mL of water was added, extraction was performed with dichloromethane. The extract was concentrated and refined through a column chromatography with silica gel and thus results in 1.5 g of yellow powder. The following is the results of 1H-NMR analysis.

Workup

  1. customfor 2 hours
  2. temperatureunder reflux for one day
  3. temperaturerefluxed for 30 minutes
  4. temperatureAfter cooling
  5. customthe product was separated out through
  6. filtrationa filter
  7. washsubsequently rinsed with methanol
  8. customthus resulting in a red powder
  9. stirringstirred for one hour
  10. stirringstirred at 65° C. for one day
  11. extractionextraction
  12. concentrationThe extract was concentrated

Sources & evidence

ORD record
ord-b341ee959f5b47c4bd72596155fc1681
Source dataset
uspto-grants-2004_10
Patent number
US06805978B2

Linked notes

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