p-Toluenesulfonic acid → 1-Cyclohexyl-6-(3-formyl-1-pyrrolyl)-7-nitro-2,3(1H,4H)-quinoxalinedione

HRID 1458871Notes

Reaction equation

HRID 1458871 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([NH:6][C:7](=[O:19])[C:8](=[O:18])[N:9]2C2CCCCC2)=[CH:4][C:3]=1[N+:20]([O-:22])=[O:21].[CH:23]([CH:25]1[CH2:29][CH:28](OC)O[CH:26]1OC)=[O:24].[C:34]1(C)[CH:39]=[CH:38][C:37](S(O)(=O)=O)=[CH:36][CH:35]=1>CN(C)C=O.C1(C)C=CC=CC=1>[CH:34]1([N:6]2[C:5]3[C:10](=[CH:11][C:2]([N:1]4[CH:28]=[CH:29][C:25]([CH:23]=[O:24])=[CH:26]4)=[C:3]([N+:20]([O-:22])=[O:21])[CH:4]=3)[NH:9][C:8](=[O:18])[C:7]2=[O:19])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 567310Tetrahydro-2,5-dimethoxyfuran-3-carbaldehydeHCID 220970767-Amino-1-cyclohexyl-6-nitro-2,3(1H,4H)-quinoxalinedione

Product 1

HCID 220972041-Cyclohexyl-6-(3-formyl-1-pyrrolyl)-7-nitro-2,3(1H,4H)-quinoxalinedioneYield 22%

Reagents, catalysts & solvents 1

HCID 21735183Dimethylformamide tolueneSolvent

Procedure

4 g (13 mmol) of the product 37b, 2.3 g (14 mmol) of 3-formyl-2,5-dimethoxytetrahydrofuran and a spatula tip of 4-toluenesulfonic acid in 200 ml of dimethylformamide/toluene (1:1) were refluxed with a water trap. After the reaction was complete (TLC check), the mixture was concentrated under reduced pressure, and the residue was partitioned between ethyl acetate and water. The organic phase was dried and concentrated under reduced pressure. This residue was purified by chromatography on silica gel (mobile phase: toluene/acetone/glacial acetic acid=40/20/1) to yield 1.1 g (22%) of the product.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe organic phase was dried
  4. concentrationconcentrated under reduced pressure
  5. customThis residue was purified by chromatography on silica gel (mobile phase: toluene/acetone/glacial acetic acid=40/20/1)

Sources & evidence

ORD record
ord-943720297c4f4a73a3edce4ed2607d99
Source dataset
uspto-grants-1998_12
Patent number
US05852017

Reaction notes

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