Iodine → HCID 14281037, compound

HRID 867495Notes

Reaction equation

HRID 867495 reaction equation
[CH3:1][CH:2]([N:4]1[CH2:8][CH:7]([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)[O:6][C:5]1=[O:28])[CH3:3].CO.II>CN(C)C=O.[Pd]>[CH3:1][CH:2]([N:4]1[CH2:8][CH:7]([CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]3[N:25]=[C:19]4[NH:20][C:21](=[O:23])[NH:22][C:18]4=[CH:17][C:15]=3[CH:16]=2)[O:6][C:5]1=[O:28])[CH3:3]

Participants

6

Reactant 3

HCID 807IodineHCID 887MethanolHCID 54280575HCID 54280575, compound

Product 1

HCID 14281037HCID 14281037, compoundYield 55.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-[[5-[[[3-(1-methylethyl)-2-oxooxazolidin-5-yl]methyl]oxy]-2-nitrophenyl]methylene]-2,4-imidazolidinedione (8.80 g, 22 mmol) in dimethylformamide (150 mL) was hydrogenated at 60 p.s.i. over 10% palladium on charcoal (0.88 g) in a low pressure hydrogenation apparatus. After 21 hours, the mixture was filtered through kieselguhr and the solvent evaporated in vacuo at about 40° C. to leave a foamy solid. Methanol (180 mL) was added, the mixture heated to reflux and iodine (5.72 g 22 mmol) added portionwise over 15 minutes. After refluxing for a further 15 minutes, the mixture was concentrated to about 50 mL and diluted with 10% sodium sulfate solution and 10% sodium carbonate solution. A grey solid was filtered off, washed with water and air dried to give (4.18 g, 54%) of product. Three further crops amounting to (3.41 g, 46%) were subsequently collected. An analytical sample was purified by dissolving 2 g in 10% hydrochloric acid in methanol. Addition of diethyl ether afforded 1,3-dihydro-7-[[3-(1-methylethyl)-2-oxo-5-oxazolidinyl]methoxy]-2H-imidazo[4,5-b]quinolin-2-one hydrochloride (1.1 g, 50%) m.p. 264°-266° C.

Workup

  1. filtrationthe mixture was filtered through kieselguhr
  2. customthe solvent evaporated in vacuo at about 40° C.
  3. customto leave a foamy solid
  4. temperaturethe mixture heated
  5. temperatureto reflux
  6. temperatureAfter refluxing for a further 15 minutes
  7. concentrationthe mixture was concentrated to about 50 mL
  8. additiondiluted with 10% sodium sulfate solution and 10% sodium carbonate solution
  9. filtrationA grey solid was filtered off
  10. washwashed with water and air
  11. customdried

Sources & evidence

ORD record
ord-5f31703cbead47ffb5b5a109234ad03b
Source dataset
uspto-grants-1988_10
Patent number
US04775674

Reaction notes

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