HCID 13300354, compound → HCID 20463646, compound

HRID 325989Notes

Reaction equation

HRID 325989 reaction equation
[CH3:1][N:2]1[CH:6]([CH3:7])[CH:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)[CH2:4][C:3]1=[O:17]>CO.[Pd]>[CH3:1][N:2]1[CH:6]([CH3:7])[CH:5]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH2:4][C:3]1=[O:17]

Participants

4

Reactant 1

HCID 13300354HCID 13300354, compound

Product 1

HCID 20463646HCID 20463646, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4.89 g (20.9 mmoles) of Ir in 50 ml of methanol and 0.49 g of 10% palladium on charcoal are placed into a 250 ml hydrogenation flask and hydrogenated at room temperature for 30 hr. The catalyst is filtered off and the methanol evaporated in vacuo. The resulting 1,5-dimethyl-4-(4'-aminophenyl)-pyrrolidin-2-one (Is), isolated in 100% yield, is dissolved in 12 ml of 18% hydrochloric acid in a 250 ml beaker and dropwise treated with 5.23 ml of 4 N sodium nitrite solution at 0°-5° C. After 5 min at 0° C. the excess nitrite was destroyed with urea. After 10 min at 0°-5° C. the diazonium solution was added dropwise to a freshly prepared solution of CuCl (20.9 mmoles) in 8 ml of 37% hydrochloric acid at 0° C. A brown precipitate forms immediately which is warmed to 60° C. for 1 hr. Extraction with chloroform and washing with water gave 4.30 g of crude reaction product after evaporation. After filtration through 130 g of silicagel 3.80 g (81%) of It were recovered as a gum.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe methanol evaporated in vacuo

Sources & evidence

ORD record
ord-795b9f677fcb4be197cc427e156184c5
Source dataset
uspto-grants-1984_04
Patent number
US04443616

Reaction notes

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