6-butyl-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione → 7-Hydroxy-7-phenyl-6-(n-butyl)-6,7-dihydropyrrolo[3,4-b]pyridin-5-one

HRID 861967Notes

Reaction equation

HRID 861967 reaction equation
[CH2:1]([N:5]1[C:13](=[O:14])[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15])[CH2:2][CH2:3][CH3:4].[C:16]1([Mg]Cl)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[OH:15][C:6]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:12]2[C:13](=[O:14])[N:5]1[CH2:1][CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 3034656-butyl-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dioneHCID 178478979HCID 178478979, compound

Product 1

HCID 197009447-Hydroxy-7-phenyl-6-(n-butyl)-6,7-dihydropyrrolo[3,4-b]pyridin-5-oneYield 90.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-65 °C

Procedure

6-(n-Butyl)-pyrrolo[3,4-b]pyridine-5,7-dione(40.4 g, 198 mmoles) was dissolved in toluene (1 L) and cooled to -65° C. Phenylmagnesium chloride (100 mL, 2M in THF, 200 moles) was added over 15 minutes. The cooling bath was then removed and the mixture allowed to warm to -10° C. The reaction was quenched by addition of 25 mL of saturated ammonium chloride solution. The room temperature solution was diluted with 500 mL of ethyl acetate and 500 mL of water. The layers were separated. Removal of most of the organic solvent was accomplished by atmospheric distillation. When the remaining volume reaches 150 mL the mixture was cooled to below 80 C and 1 L of hexanes was added. The resulting crystalline mass was filtered and dried to give 50.6 g of 7-hydroxy-7-phenyl-6-(n-butyl)-6,7-dihydropyrrolo[3,4-b]pyridin-5-one.

Workup

  1. customThe cooling bath was then removed
  2. temperatureto warm to -10° C
  3. customThe reaction was quenched by addition of 25 mL of saturated ammonium chloride solution
  4. additionThe room temperature solution was diluted with 500 mL of ethyl acetate and 500 mL of water
  5. customThe layers were separated
  6. customRemoval of most of the organic solvent
  7. distillationwas accomplished by atmospheric distillation
  8. temperaturewas cooled to below 80 C and 1 L of hexanes
  9. additionwas added
  10. filtrationThe resulting crystalline mass was filtered
  11. customdried

Sources & evidence

ORD record
ord-5663b16ef6584c90b59e80b0c92f72b3
Source dataset
uspto-grants-1998_02
Patent number
US05716954

Reaction notes

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