Iodine → HCID 14281033, compound

HRID 867492Notes

Reaction equation

HRID 867492 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][O:14]C2CCCCO2)=[CH:6][C:5]=1[CH:21]=[C:22]1[NH:26][C:25](=[O:27])[NH:24][C:23]1=O)([O-])=O.CO.II>CN(C)C=O.[Pd]>[OH:14][CH2:13][CH2:12][CH2:11][O:10][C:7]1[CH:8]=[CH:9][C:4]2[N:1]=[C:23]3[NH:24][C:25](=[O:27])[NH:26][C:22]3=[CH:21][C:5]=2[CH:6]=1

Participants

6

Reactant 3

HCID 807IodineHCID 887MethanolHCID 54277078HCID 54277078, compound

Product 1

HCID 14281033HCID 14281033, compoundYield 33.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-[[2-nitro-5-[3-[(tetrahydro-2H-pyran-2-yl)oxy]propoxy]phenyl]methylene]-2,4-imidazolidinedione (19.14 g, 49 mmol) in dimethylformamide (150 mL) was hydrogenated over 10% palladium on charcoal (2 g) at 55 p.s.i. in a low pressure hydrogenation apparatus. After 23 hours, the mixture was filtered through kieselguhr and concentrated in vacuo. The resultant yellow solid was dissolved in refluxing methanol (300 mL) and iodine (11.74 g, 49 mmol) added portionwise. After 15 minutes, the mixture was concentrated to dryness and the residue diluted with 10% sodium thiosulfate solution and 10% sodium carbonate solution. The solid was filtered off, washed with water and dried in air. Crystallization from aqueous dimethylformamide afforded 1,3-dihydro-7-(3-hydroxypropoxy)-2H-imidazo[4,5-b]quinolin-2-one (4.22 g, 33%), m.p. 343°-345° C. (dec.).

Workup

  1. filtrationthe mixture was filtered through kieselguhr
  2. concentrationconcentrated in vacuo
  3. dissolutionThe resultant yellow solid was dissolved
  4. additionadded portionwise
  5. waitAfter 15 minutes
  6. concentrationthe mixture was concentrated to dryness
  7. additionthe residue diluted with 10% sodium thiosulfate solution and 10% sodium carbonate solution
  8. filtrationThe solid was filtered off
  9. washwashed with water
  10. customdried in air
  11. customCrystallization from aqueous dimethylformamide

Sources & evidence

ORD record
ord-3cebc98c44c843c3bc5d721eb21cd856
Source dataset
uspto-grants-1988_10
Patent number
US04775674

Reaction notes

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