Peracetic Acid → HCID 67381857, compound

HRID 909356Notes

Reaction equation

HRID 909356 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]([CH2:15][CH2:16][CH2:17][O:18][CH:19]([CH3:21])[CH3:20])[C:13]([CH2:22][O:23][CH2:24][CH3:25])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1.C(OO)(=[O:28])C.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]([CH2:15][CH2:16][CH2:17][O:18][CH:19]([CH3:20])[CH3:21])[C:13]([CH2:22][O:23][CH2:24][CH3:25])=[N:12][C:7]=3[CH:8]=[N+:9]([O-:28])[C:10]=2[CH:11]=1

Participants

7

Reactant 4

HCID 6585Peracetic Acid2×HCID 516892Sodium BicarbonateHCID 656671Sodium Pyrosulfite2×HCID 673819647-Bromo-2-ethoxymethyl-1-(isopropoxypropyl)-1H-imidazo[4,5-c]quinoline

Product 1

HCID 67381857HCID 67381857, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A slurry of 7-bromo-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinoline (6.6 g, 16.2 mmol) in ethyl acetate (55 mL) was heated to 50° C. Peroxyacetic acid (5.12 mL, 24.4 mmol, of 32% in dilute acetic acid) was added dropwise over a period of 2 minutes. The reaction was allowed to stir at 50° C. for 2 hours. Additional peroxyacetic acid (1 mL) was added and the reaction mixture was stirred for an additional 2 hours. A solution of sodium metabisulfite (4.01 g, 21.1 mmol) in water (8 mL) was added. Following the addition of the sodium metabisulfite, the pH of the reaction mixture was adjusted to pH 10 with aqueous saturated sodium bicarbonate. The layers were separated and the aqueous layer was extracted with dichloromethane (2×50 mL). The combined organics were washed sequentially with water and brine, dried over sodium sulfate, filtered, and then concentrated under reduced pressure to provide a yellow solid. This material was purified by flash chromatography (150 g of silica gel eluting with a gradient of 1-12% CMA in chloroform) to provide 5.49 g of 7-bromo-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinoline-5-oxide.

Workup

  1. stirringthe reaction mixture was stirred for an additional 2 hours
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with dichloromethane (2×50 mL)
  4. washThe combined organics were washed sequentially with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto provide a yellow solid
  9. customThis material was purified by flash chromatography (150 g of silica gel eluting with a gradient of 1-12% CMA in chloroform)

Sources & evidence

ORD record
ord-941db52975014e29990783f513a6a7c5
Source dataset
uspto-grants-2011_09
Patent number
US08017779B2

Reaction notes

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