Toluene → HCID 67506527, compound

HRID 2105485Notes

Reaction equation

HRID 2105485 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N:12]=[CH:13][N:14](C)C.Cl.[CH:18]([O:21]N)([CH3:20])[CH3:19].C(N(CC)CC)C.C1(C)C=CC=CC=1>C(O)C>[CH:18]([O:21][N:14]1[C:2]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N:5]=[CH:4][C:3]=2[N:12]=[CH:13]1)([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 12696235O-(propan-2-yl)hydroxylamine hydrochloride3×HCID 67506192HCID 67506192, compound

Product 1

HCID 67506527HCID 67506527, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of N′-(4-chloroquinolin-3-yl)-N,N-dimethylimidoformamide (9.3 g, 0.040 mol) and O-isopropylhydroxylamine hydrochloride (5.0 g, 45 mmol) in ethanol (150 mL) was heated at reflux overnight. An analysis by LC/MS indicated the reaction was incomplete, and triethylamine (2.0 mL) was added. The reaction was heated at reflux for three hours and found to be incomplete. The ethanol was removed under reduced pressure, and toluene (150 mL) was added. The reaction was heated at reflux overnight but was found again to be incomplete. The toluene was removed under reduced pressure, and ethanol (150 mL) and additional O-isopropylhydroxylamine hydrochloride (1.0 g, 9.0 mmol) were added. The reaction was heated at reflux over night with additional O-isopropylhydroxylamine hydrochloride (0.5 g) added after three hours and again (0.4 g) after five hours. The work-up and purification procedures described in Part C of Example 19 were followed with the modification that chromatographic purification was carried out eluting with 5% methanol in dichloromethane containing 3 mL of aqueous ammonium hydroxide per liter of eluent. 1-Isopropoxy-1H-imidazo[4,5-c]quinoline (7.1 g) was obtained as a light red solid.

Workup

  1. temperatureat reflux overnight
  2. temperatureThe reaction was heated
  3. temperatureat reflux for three hours
  4. customThe ethanol was removed under reduced pressure, and toluene (150 mL)
  5. additionwas added
  6. temperatureThe reaction was heated
  7. temperatureat reflux overnight
  8. additionwere added
  9. temperatureThe reaction was heated
  10. additionadded after three hours
  11. customThe work-up and purification procedures
  12. customwere followed with the modification that chromatographic purification
  13. washwas carried out eluting with 5% methanol in dichloromethane containing 3 mL of aqueous ammonium hydroxide per liter of eluent

Sources & evidence

ORD record
ord-9476dca1f3724b909ee21639fa1caa8f
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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