Iodine → HCID 14281031, compound

HRID 867491Notes

Reaction equation

HRID 867491 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([N+:21]([O-])=O)=[C:11]([CH:13]=[C:14]2[NH:18][C:17](=[O:19])[NH:16][C:15]2=O)[CH:12]=1)[CH3:2].CO.II>CN(C)C=O.[Pd]>[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[N:21]=[C:15]3[NH:16][C:17](=[O:19])[NH:18][C:14]3=[CH:13][C:11]=2[CH:12]=1)[CH3:2]

Participants

6

Reactant 3

HCID 807IodineHCID 887MethanolHCID 54052585HCID 54052585, compound

Product 1

HCID 14281031HCID 14281031, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-[[5-(2-ethoxyethoxy)-2-nitrophenyl]methylene]-2,4-imidazolidinedione (10.60 g, 33 mmol) in dimethylformamide (120 mL) was hydrogenated over 10% palladium on charcoal (1 g) at 50 p.s.i. in a low pressure hydrogenation apparatus. After 23 hours, the mixture was filtered through kieselguhr and the solvent evaporated to leave a solid which was suspended in refluxing methanol (200 mL) and treated with iodine (8.38 g, 33 mmol) added portionwise. After 15 minutes the mixture was concentrated to about 50 mL and diluted with 10% sodium thiosulfate solution and 10% sodium carbonate solution. The mixture was stirred for 15 minutes and the solid filtered off, washed with water and dried in air before being dissolved in a solution of 10% hydrogen chloride in methanol. Addition of diethyl ether precipitated 7-(2-ethoxyethoxy)-1,3-dihydro-2H-imidazo[4,5-b]quinolin-2-one hydrochloride (4.52 g, 56%), m.p. 290°-293° C. (dec.).

Workup

  1. filtrationthe mixture was filtered through kieselguhr
  2. customthe solvent evaporated
  3. customto leave a solid which
  4. additionadded portionwise
  5. concentrationAfter 15 minutes the mixture was concentrated to about 50 mL
  6. additiondiluted with 10% sodium thiosulfate solution and 10% sodium carbonate solution
  7. filtrationthe solid filtered off
  8. washwashed with water
  9. customdried in air
  10. dissolutionbefore being dissolved in a solution of 10% hydrogen chloride in methanol
  11. additionAddition of diethyl ether
  12. customprecipitated 7-(2-ethoxyethoxy)-1,3-dihydro-2H-imidazo[4,5-b]quinolin-2-one hydrochloride (4.52 g, 56%), m.p. 290°-293° C. (dec.)

Sources & evidence

ORD record
ord-114464b3f8fb45dd9eff30b818aa0033
Source dataset
uspto-grants-1988_10
Patent number
US04775674

Reaction notes

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