N-Hydroxyphthalimide → HCID 68537604, compound

HRID 1187389Notes

Reaction equation

HRID 1187389 reaction equation
[CH2:1]([C:4]1[N:5]([CH2:17][CH2:18][CH2:19][OH:20])[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=1)[CH2:2][CH3:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[N:41]1[C:45](=[O:46])[C:44]2=[CH:47][CH:48]=[CH:49][CH:50]=[C:43]2[C:42]1=[O:51].N(C(OC(C)C)=O)=NC(OC(C)C)=O.C(=O)(O)[O-].[Na+]>O1CCCC1.O.C(Cl)(Cl)Cl>[CH2:1]([C:4]1[N:5]([CH2:17][CH2:18][CH2:19][O:20][N:41]2[C:45](=[O:46])[C:44]3[C:43](=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:42]2=[O:51])[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=1)[CH2:2][CH3:3]

Participants

9

Reactant 5

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 516892Sodium BicarbonateHCID 68537722HCID 68537722, compound

Product 1

HCID 68537604HCID 68537604, compoundYield 92.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)propan-1-ol (20.0 grams (g), 74.3 millimoles (mmol)) in tetrahydrofuran (300 milliliters (mL)) was cooled to approximately 0° C.; triphenylphosphine (23.4 g, 89.1 mmol) and N-hydroxyphthalimide (14.5 g, 89.1 mmol) were then added. After five minutes of stinring, diisopropyl azodicarboxylate (17.5 mL, 89.1 mmol) was added dropwise over a period of 15 minutes (min). The reaction was allowed to warm to room temperature and stirred overnight. The solvent was removed under reduced pressure, and the residue was dissolved in chloroform (300 mL). A solution of hydrochloric acid (150 mL of 6 molar (M) was then added, and approximately 50 mL of the solvent was removed under reduced pressure to provide a white precipitate, which was stirred for ten minutes and isolated by filtration. Additional salt eventually precipitated from the filtrate and was isolated by filtration. Chloroform (300 mL) and water (300 mL) were added to the salt, and solid sodium bicarbonate was added to the mixture to adjust to pH 8. The organic solution was then dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 28.4 g of 2-[3-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)propoxy]-1H-isoindole-1,3(2H)-dione as a white solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in chloroform (300 mL)
  3. additionA solution of hydrochloric acid (150 mL of 6 molar (M) was then added
  4. customapproximately 50 mL of the solvent was removed under reduced pressure
  5. customto provide a white precipitate, which
  6. stirringwas stirred for ten minutes
  7. customisolated by filtration
  8. customAdditional salt eventually precipitated from the filtrate
  9. customwas isolated by filtration
  10. additionwas added to the mixture
  11. dry with materialThe organic solution was then dried over magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f367f064792f44d888985861fc2cd0f8
Source dataset
uspto-grants-2014_03
Patent number
US08673932B2

Reaction notes

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