Iodine → 7-(4-Oxo-pentyloxy)-1,3-dihydro-imidazo[4,5-b]quinolin-2-one

HRID 867493Notes

Reaction equation

HRID 867493 reaction equation
[CH3:1][C:2]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]([N+:25]([O-])=O)=[C:15]([CH:17]=[C:18]3[NH:22][C:21](=[O:23])[NH:20][C:19]3=O)[CH:16]=2)OCC[O:3]1.CO.II>CN(C)C=O.[Pd].S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>[O:3]=[C:2]([CH3:1])[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]2[N:25]=[C:19]3[NH:20][C:21](=[O:23])[NH:22][C:18]3=[CH:17][C:15]=2[CH:16]=1

Participants

8

Reactant 3

HCID 807IodineHCID 887MethanolHCID 537342405-[[5-[3-(2-Methyl-1,3-dioxolan-2-yl)propoxy]-2-nitrophenyl]methylene]-2,4-imidazolidinedione

Product 1

HCID 142810207-(4-Oxo-pentyloxy)-1,3-dihydro-imidazo[4,5-b]quinolin-2-oneYield 84.2%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 10340Sodium CarbonateSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

A solution of 5-[[5-[3-(2-methyl-1,3-dioxolan-2-yl)propoxy]-2-nitrophenyl]methylene]-2,4-imidazolidinedione (34.7 g, 92 mmol) in dimethylformamide (500 mL) was hydrogenated over 10% palladium on charcoal (3.5 g) at 200 p.s.i. in a low pressure hydrogenator. After 18 hours, the mixture was filtered through kieselguhr and concentrated in vacuo to afford a beige solid which was suspended in refluxing methanol (500 mL). Iodine (23.3 g, 92 mmol) was added portionwise and the mixture heated at reflux for a further 30 minutes before being cooled and diluted with 10% sodium thiosulfate solution (230 mL) and 10% sodium carbonate solution (75 mL). The mixture was concentrated to a volume of approximately 400 mL, the precipitate filtered off, washed with water and dried in vacuo of 70° C. to afford 1,3-dihydro-7-(4-oxopentoxy)-2H-imidazo[4,5-b]quinolin-2-one (22.1 g, 84%). An analytical sample was prepared by crystallizing a 10 g portion from aqueous dimethylformamide to give 7.8 g of pure material which had m.p. 294°-296° C. (dec.).

Workup

  1. filtrationthe mixture was filtered through kieselguhr
  2. concentrationconcentrated in vacuo
  3. customto afford a beige solid which
  4. temperaturethe mixture heated
  5. temperatureat reflux for a further 30 minutes
  6. temperaturebefore being cooled
  7. concentrationThe mixture was concentrated to a volume of approximately 400 mL
  8. filtrationthe precipitate filtered off
  9. washwashed with water
  10. customdried in vacuo of 70° C.

Sources & evidence

ORD record
ord-acd5aa75ee184bc6975b81a98c017e2c
Source dataset
uspto-grants-1988_10
Patent number
US04775674

Reaction notes

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