Acetic Acid → HCID 69205037, compound

HRID 1373904Notes

Reaction equation

HRID 1373904 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([NH2:18])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:2].[C:19](O)(=O)[CH3:20].[C:23](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[BH4-].[Na+]>ClCCCl.CO.CC(C)=O>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([NH:18][CH:19]([CH3:20])[CH3:23])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:2]

Participants

8

Reactant 4

HCID 176Acetic Acid2×HCID 4311764Sodium borohydrideHCID 5049666Sodium triacetoxyborohydride2×HCID 21075716HCID 21075716, compound

Product 1

HCID 69205037HCID 69205037, compoundYield 33.5%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 180AcetoneSolvent2×HCID 887MethanolSolvent

Procedure

A solution of 2-ethoxymethy-1H-imidazo[4,5-c]quinolin-1-amine (2.50 g, 10.3 mmol) in 250 mL of 1,2-dichloroethane was treated with acetone (0.83 mL, 11.3 mmol), acetic acid (0.65 mL, 11.3 mmol) and sodium triacetoxyborohydride (2.39 g, 11.3 mL). After stirring overnight, additional acetone (5 mL), acetic acid (0.65 mL, 11.3 mmol) and sodium triacetoxyborohydride (2.39 g, 11.3 mL) were added. After 2 d, the reaction was carefully quenched by addition of saturated NaHCO3 solution. The layers were separated and the aqueous portion was extracted with additional CH2Cl2. The combined organic layers were washed with H2O and brine, dried over Na2SO4, and concentrated under reduced pressure to give a brown oil. Some isopropylidene intermediate was still present, so the material was dissolved in 50 mL of MeOH and treated with NaBH4 (1.0 g). After 2 h, the reaction was quenched by the addition of H2O and the reaction mixture was concentrated under reduced pressure. The residue was partitioned between saturated NaHCO3 solution and CH2Cl2. The layers were separated and the organic portion was washed with saturated NaHCO3, H2O and brine. The organic portion was dried over Na2SO4, filtered, and concentrated under reduced pressure. Chromatography (SiO2, 4% MeOH/CHCl3) gave N-(2-ethoxymethy-1H-imidazo[4,5-c]quinolin-1-yl)isopropylamine (0.98 g) as a brown oil.

Workup

  1. waitAfter 2 d
  2. customthe reaction was carefully quenched by addition of saturated NaHCO3 solution
  3. customThe layers were separated
  4. extractionthe aqueous portion was extracted with additional CH2Cl2
  5. washThe combined organic layers were washed with H2O and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto give a brown oil
  9. waitAfter 2 h
  10. customthe reaction was quenched by the addition of H2O
  11. concentrationthe reaction mixture was concentrated under reduced pressure
  12. customThe residue was partitioned between saturated NaHCO3 solution and CH2Cl2
  13. customThe layers were separated
  14. washthe organic portion was washed with saturated NaHCO3, H2O and brine
  15. dry with materialThe organic portion was dried over Na2SO4
  16. filtrationfiltered
  17. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0f34bc35b9a84a2e8c4c218b37a76df6
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

Loading…